PGP™ Desktop For Mac OS X User's Guide 10.2 Macintosh Pgp 1020 Users En

User Manual: Desktop - 10.2 - Macintosh - User's Guide User Guide for PGP Desktop Software, Free Instruction Manual

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PGP™ Desktop for Mac OS X
User's Guide
10.2

The software described in this book is furnished under a license agreement and may be used only in accordance with the terms of the agreement.
Version 10.2.0. Last updated: July 2011.

Legal Notice
Copyright (c) 2011 Symantec Corporation. All rights reserved.
Symantec, the Symantec Logo, PGP, Pretty Good Privacy, and the PGP logo are trademarks or registered trademarks of Symantec Corporation or its
affiliates in the U.S. and other countries. Other names may be trademarks of their respective owners.
The product described in this document is distributed under licenses restricting its use, copying, distribution, and decompilation/reverse engineering.
No part of this document may be reproduced in any form by any means without prior written authorization of Symantec Corporation and its licensors, if
any.
THE DOCUMENTATION IS PROVIDED"AS IS"AND ALL EXPRESS OR IMPLIED CONDITIONS, REPRESENTATIONS AND WARRANTIES, INCLUDING
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The Licensed Software and Documentation are deemed to be commercial computer software as defined in FAR 12.212 and subject to restricted rights
as defined in FAR Section 52.227-19 "Commercial Computer Software - Restricted Rights" and DFARS 227.7202, et seq. “Commercial Computer
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Symantec Corporation
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Printed in the United States of America.
10 9 8 7 6 5 4 3 2 1

Contents
About PGP Desktop 10.2 for Mac OS X
What's New in PGP Desktop Version 10.2 for Mac OS X
Using this Guide
“Managed” versus “Unmanaged” Users
Conventions Used in This Guide
Who Should Read This Document
About PGP Desktop Licensing
About PGP Desktop Licensing
Checking License Details
If Your License Has Expired
Technical Support
Contacting Technical Support
Licensing and registration
Customer service
Support agreement resources

PGP Desktop Basics
PGP Desktop Terminology
PGP Product Components
Terms Used in PGP Desktop
Conventional and Public Key Cryptography
Using PGP Desktop for the First Time

Installing PGP Desktop
System Requirements
Installing and Configuring PGP Desktop
Installing the Software
Using PGP Desktop with Apple Boot Camp
Upgrading the Software
Licensing PGP Desktop
Running the Setup Assistant
Integrating with Entourage 2008
Uninstalling PGP Desktop
Moving Your PGP Desktop Installation from One Computer to Another

The PGP Desktop User Interface
Accessing PGP Desktop Features
PGP Desktop Main Screen
Using the PGP Desktop Icon in the Menu Bar
Using the PGP Dock Icon
Using the Mac OS X Finder
PGP Desktop Notifier alerts
PGP Desktop Notifier for Messaging
PGP Desktop and the Finder
Overview

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Encrypt, Sign, or Encrypt and Sign
Shred
Decrypt/Verify
Mount or Unmount a PGP Virtual Disk Volume
Import a PGP Key
Add PGP Public Keys to Your Keyring
Extract the Contents of a PGP Zip Archive
Viewing the PGP Log

Working with PGP Keys
Viewing Keys
Creating a Smart Keyring
Creating a Keypair
Expert Mode Key Settings
Protecting Your Private Key
Protecting Keys and Keyrings
Backing up Your Private Key
What if You Lose Your Key?
Distributing Your Public Key
Placing Your Public Key on a Keyserver
Including Your Public Key in an Email Message
Exporting Your Public Key to a File
Getting the Public Keys of Others
Getting Public Keys from a Keyserver
Getting Public Keys from Email Messages
Working with Keyservers
Using Master Keys
Adding Keys to the Master Key List
Deleting Keys from the Master Key List

Managing PGP Keys
Examining and Setting Key Properties
Adding and Removing Photographs
Managing User Names and Email Addresses on a Key
Importing Keys and X.509 Certificates
Importing X.509 Certificates Included in S/MIME Email Messages
Changing Your Passphrase
Deleting Keys, User IDs, and Signatures
Disabling and Enabling Public Keys
Verifying a Public Key
Signing a Public Key
Revoking Your Signature from a Public Key
Granting Trust for Key Validations
To grant trust to a key
Working with Subkeys
Using Separate Subkeys
Viewing Subkeys
Creating New Subkeys
Specifying Key Usage for Subkeys
Revoking Subkeys
Removing Subkeys

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Working with ADKs
Adding an ADK to a Keypair
Updating an ADK
Removing an ADK
Working with Revokers
Appointing a Designated Revoker
Revoking a Key
Splitting and Rejoining Keys
Creating a Split Key
Rejoining Split Keys
If You Lost Your Key or Passphrase
Reconstructing Keys with PGP Universal Server
Creating Key Reconstruction Data
Reconstructing Your Key if You Lost Your Key or Passphrase
Protecting Your Keys

Securing Email Messages
How PGP Desktop Secures Email Messages
Incoming Messages
Understanding Annotations on Incoming Messages
Outgoing Messages
Securing Sent Items on IMAP Email Servers
Using Offline Policy
Services and Policies
Viewing Services and Policies
Creating a New Messaging Service
Editing Message Service Properties
Disabling or Enabling a Service
Deleting a Service
Multiple Services
Troubleshooting PGP Messaging Services
Creating a New Security Policy
Regular Expressions in Policies
Security Policy Information and Examples
Working with the Security Policy List
Editing a Security Policy
Editing a Mailing List Policy
Deleting a Security Policy
Changing the Order of Policies in the List
PGP Desktop and SSL
Key Modes
Determining Key Mode
Changing Key Mode
Viewing the PGP Log
Using PGP Scripts with Entourage 2008

Securing Instant Messaging
About PGP Desktop Instant Messaging Compatibility
Instant Messaging Client Compatibility
About the Keys Used for Encryption
Encrypting your IM Sessions

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iii

Contents

Viewing Email with PGP Viewer

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Overview of PGP Viewer
Supported Email Clients
Opening an Encrypted Email Message or File
Copying Email Messages to Your Inbox
Exporting Email Messages
PGP Viewer Preferences
Security Features in PGP Viewer

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Protecting Disks with PGP Whole Disk Encryption

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About PGP Whole Disk Encryption
Encrypting Boot Disks
How does PGP WDE Differ from PGP Virtual Disk?
Licensing PGP Whole Disk Encryption
License Expiration
Prepare Your Disk for Encryption
Supported Disk Types
Supported Keyboards
Ensure Disk Health Before Encryption
Calculate the Encryption Duration
Run a Pilot Test to Ensure Software Compatibility
Determine the Authentication Method for the Disk
Encrypting a Disk
Supported Characters
Encrypting the Disk
Encountering Disk Errors During Encryption
Using a PGP-WDE Encrypted Disk
Authenticating at the PGP BootGuard Screen
Authenticating With a User Name
Maintaining the Security of Your Disk
Viewing Key Information on an Encrypted Disk
Modifying the System Partition
Adding Other Users to an Encrypted Disk
Deleting Users From an Encrypted Disk
Changing User Passphrases
Re-Encrypting an Encrypted Disk
Backing Up and Restoring
Uninstalling PGP Desktop from Encrypted Disks
Using PGP WDE in a PGP Universal Server-Managed Environment
PGP Whole Disk Encryption Administration
Creating a Recovery Token
Using a Recovery Token
Recovering Data From an Encrypted Drive
Creating and Using Recovery Disks
Decrypting an Encrypted Disk
Moving Removable Disks to Other Systems
Accessing Data on Encrypted Removable Disks
Special Security Precautions Taken by PGP Desktop
Passphrase Erasure
Virtual Memory Protection

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Contents

Memory Static Ion Migration Protection
Other Security Considerations
Technical Details About Encrypting Boot Disks

Using PGP Virtual Disks
About PGP Virtual Disks
Creating a New PGP Virtual Disk
Viewing the Properties of a PGP Virtual Disk
Using a Mounted PGP Virtual Disk
Mounting a PGP Virtual Disk
Unmounting a PGP Virtual Disk
Set Mount Location
Compacting a PGP Virtual Disk
Re-Encrypting PGP Virtual Disks
Working with Alternate Users
Adding Alternate User Accounts to a PGP Virtual Disk
Deleting Alternate User Accounts From a PGP Virtual Disk
Disabling and Enabling Alternate User Accounts
Changing Read/Write and Read-Only Status
Granting Administrator Status to an Alternate User
Changing User Passphrases
Deleting PGP Virtual Disks
Maintaining PGP Virtual Disks
Mounting PGP Virtual Disk Volumes on a Remote Server
Backing up PGP Virtual Disk Volumes
Exchanging PGP Virtual Disks
The PGP Virtual Disk Encryption Algorithms
Special Security Precautions Taken by PGP Virtual Disk
Passphrase Erasure
Virtual Memory Protection
Memory Static Ion Migration Protection
Other Security Considerations

Accessing Mobile Data with PGP Portable
Accessing Data on a PGP Portable Disk
Changing the Passphrase for a PGP Portable Disk
Unmounting a PGP Portable Disk

Using PGP Zip
Overview
Creating PGP Zip Archives
Opening a PGP Zip Archive
Verifying Signed PGP Zip Archives

Shredding Files with PGP Shredder
Using PGP Shredder to Permanently Delete Files and Folders
Shredding Files using the PGP Shredder icon
Shredding Files using the Shred Files Icon in the PGP Desktop Toolbar

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Shredding Files using the Shred Command from the File menu
Shredding Files in the Finder

Setting Preferences

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Accessing PGP Desktop Preferences
General Preferences
Keys Preferences
Master Keys Preferences
Messaging Preferences
Proxy Options
Disk Preferences
Notifications Preferences
Advanced Preferences

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Working with Passwords and Passphrases

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Choosing whether to use a password or passphrase
The Passphrase Quality Bar
Creating Strong Passphrases
What if You Forget Your Passphrase?
Saving Your Passphrase in the Keychain

Using PGP Desktop with PGP Universal Server
Overview
For PGP Administrators
Manually binding to a PGP Universal Server

Index

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About PGP Desktop 10.2 for Mac OS X

PGP Desktop is a security tool that uses cryptography to protect your data against
unauthorized access.
PGP Desktop protects your data while being sent by email or by instant messaging (IM).
It lets you encrypt your entire hard drive or hard drive partition (on Windows
systems)—so everything is protected all the time—or just a portion of your hard drive,
via a virtual disk on which you can securely store your most sensitive data. You can use
it to share your files and folders securely with others over a network. It lets you put any
combination of files and folders into an encrypted, compressed package for easy
distribution or backup. Finally, use PGP Desktop to shred (securely delete) sensitive
files—so that no one can retrieve them—and shred free space on your hard drive, so
there are no unsecured remains of any files.
Use PGP Desktop to create PGP keypairs and manage both your personal keypairs and
the public keys of others.
To make the most of PGP Desktop, you should be familiar with PGP Desktop
Terminology (on page 9). You should also understand conventional and public-key
cryptography, as described in Conventional and Public Key Cryptography (on page 11).

In This Chapter
What's New in PGP Desktop Version 10.2 for Mac OS X........................................... 1
Using this Guide .............................................................................................................. 2
Who Should Read This Document ................................................................................ 3
About PGP Desktop Licensing ....................................................................................... 3
Technical Support ........................................................................................................... 6

What's New in PGP Desktop Version 10.2 for Mac OS X
Building on Symantec Corporation’s proven technology, PGP Desktop 10.2 for Mac OS X
includes numerous improvements and the following new and resolved features.

General
•

Symantec identity branding. The user interface and all user assistance (including
help and user’s guides) have been rebranded to include the Symantec logo and
colors. All product names remain the same. PGP Desktop for Windows and PGP
Desktop for Mac OS X.

About PGP Desktop 10.2 for Mac OS X
Using this Guide

Messaging
•

Symantec PGP Viewer for iOS. A separate application for the iPhone and iPad that
you use to read encrypted email messages on your iOS mobile device. Available at
no cost through the Apple App Store. Requires integration with PGP Universal
Server to manage keys.

PGP Whole Disk Encryption
•

AES-NI for Mac OS X and Linux systems. If your Mac OS X or Linux system
supports the Intel® Advanced Encryption Standard (AES) Instructions (AES-NI),
your system is encrypted and decrypted using the hardware associated with this
encryption algorithm. AES-NI provides improved performance during encryption
and decryption processes as well as disk I/O enhancements while your disk is
encrypted.

•

User name and domain in PGP BootGuard. If you are using PGP Desktop in a PGP
Universal Server-managed environment, your administrator can now require that
you authenticate at PGP BootGuard with your user name and domain (on Windows
systems) or user name (on Mac OS X systems). The PGP BootGuard screen displays
fields for you to enter your user name, domain, and passphrase.

•

Additional keyboard support. Added compatibility with German (Switzerland)
and German (French) keyboards for PGP WDE on Mac OS X systems.

Using this Guide
This Guide provides information on configuring and using the components within PGP
Desktop. Each chapter of the guide is devoted to one of the components of PGP Desktop.

“Managed” versus “Unmanaged” Users
A PGP Universal Server can be used to control the policies and settings used by
components of PGP Desktop. This is often the case in enterprises using PGP software.
PGP Desktop users in this configuration are known as managed users, because the
settings and policies available in their PGP Desktop software are pre-configured by a
PGP administrator and managed using a PGP Universal Server. If you are part of a
managed environment, your company may have specific usage requirements. For
example, managed users may or may not be allowed to send plaintext email, or may be
required to encrypt their disk with PGP Whole Disk Encryption.
Users not under the control of a PGP Universal Server are called unmanaged or
standalone users.
This document describes how PGP Desktop works in both situations; however, managed
users may discover while working with the product that some of the settings described
in this document are not available in their environments. For more information, see
Using PGP Desktop with PGP Universal Server (on page 185).

About PGP Desktop 10.2 for Mac OS X
Who Should Read This Document

Features Customized by Your PGP Universal Server Administrator
If you are using PGP Desktop as a "managed" user in a PGP Universal Server-managed
environment, there are some settings that can be specified by your administrator.
These settings may change the way features are displayed in PGP Desktop.
•

Disabled features. Your PGP Universal Server administrator can enable or disable
specific functionality. For example, your administrator may disable the ability to
create PGP Zip archives, or to create PGP NetShare protected folders (on Windows
systems).
When a feature is disabled, the control item in the left side is not displayed and the
menu for that feature is not available. The graphics included in this guide depict
the default installation with all features enabled. The PGP Desktop interface may
look different if your administrator has customized the features available.

Conventions Used in This Guide
Notes, Cautions, and Warnings are used in the following ways.
Notes: Notes are extra, but important, information. A Note calls your attention to
important aspects of the product. You will be able to use the product better if you
read the Notes.
Cautions: Cautions indicate the possibility of loss of data or a minor security breach.
A Caution tells you about a situation where problems could occur unless precautions
are taken. Pay attention to Cautions.
Warnings: Warnings indicate the possibility of significant data loss or a major
security breach. A Warning means serious problems are going to happen unless you
take the appropriate action. Please take Warnings very seriously.

Who Should Read This Document
This document is for anyone who is going to be using the PGP Desktop for Mac OS X
software to protect their data.

About PGP Desktop Licensing
A license is used within the PGP software to enable the functionality you purchased,
and sets the expiration of the software. Depending on the license you have, some or all
of the PGP Desktop family of applications will be active. Once you have entered the
license, you must then authorize the software with Symantec Corporation, either
manually or online.
There are three types of licenses:
•

Evaluation: This type of license is typically time-delimited and may not include all
PGP Desktop functionality.

About PGP Desktop 10.2 for Mac OS X
About PGP Desktop Licensing

•

Subscription: This type of license is typically valid for a subscription period of one
year. During the subscription period, you receive the current version of PGP
software and all upgrades and updates released during this period.

•

Perpetual: This type of license allows you to use PGP Desktop indefinitely. With
the addition of the annual Software Insurance policy, which must be renewed
annually, you also receive all upgrades and updates released during the policy
term.

About PGP Desktop Licensing
To license PGP Desktop
Do one of the following:
•

If you are a managed user, you are most likely already using a licensed copy of PGP
Desktop. Check your license details as described in Checking License Details (on
page 4). If you have questions, please contact your PGP administrator.

•

If you are an unmanaged user, or a PGP administrator, check your license details
as described in Checking License Details (on page 4). If you need to authorize your
copy of PGP Desktop, do so as described in Authorizing PGP Desktop for Mac OS X
(see "Authorizing PGP Desktop or Mac OS X" on page 5).

Checking License Details
To see the details of your PGP Desktop license:
1

Open PGP Desktop.

From the PGP menu, select License. The License Information dialog box is
displayed. This dialog box displays:

•

Name: The name your license is registered to.

•

Organization: The organization your license is registered to.

•

Email: The email address associated with your license.

•

Type: The type of license you have, Enterprise or Home.

Click Details. The details of your license are displayed.

About PGP Desktop 10.2 for Mac OS X
About PGP Desktop Licensing

•

Expiration Date: The date your license expires.

•

Number of Seats: The number of seats available for this license.

•

Enabled Features: The components that are active in your license.

•

Disabled Features: The components that are not active in your license.

Note: If you do not authorize your copy of PGP Desktop, only limited features are
available to you (PGP Zip and Keys).

Authorizing PGP Desktop or Mac OS X
If you need to change to a new license number, or if you skipped the license
authorization process during configuration, follow these instructions to authorize your
software.
Before you begin
If you purchased PGP Desktop, you received an order confirmation with licensing
information.
1

OpenPGP Desktop.

From the PGP menu, select License.

Click Change License.

Type the Name and Organization exactly as specified in your order confirmation.

Type the Email address you want to assign to the licensing of the product.

Do one of the following:
•

Type your 28-character license number in the License Number fields (for
example, DEMO1-DEMO2-DEMO3-DEMO4-DEMO5-ABC).

Note: To avoid typing errors and make the authorization easier, copy the entire
license number, put the cursor in the first “License Number” field, and paste.
Your license number will be correctly entered into all six License Number fields.
•

To purchase a PGP Desktop license, select Purchase Now. A Web browser
opens so you can access the online PGP Store.

Click Authorize.

When your license is authorized, click OK to complete the process.

Resolving License Authorization Errors
If you receive any error messages while authorizing your software, the ways to resolve
this issue vary based on the error message. See the HOWTO: License PGP Desktop 10.2
section in the PGP Support Portal (https://support.pgp.com) for suggestions.

About PGP Desktop 10.2 for Mac OS X
Technical Support

If Your License Has Expired
If your PGP Desktop license has expired, you will receive a PGP License Expiration
message when you launch PGP Desktop. See the following sections for information on
how an expired license affects the functionality of PGP Desktop.

PGP Desktop Email
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Outgoing email messages are no longer sent encrypted.

•

PGP Virtual Disks are still accessible in Read-Only mode. Read-Only allows data to
be copied from a PGP Virtual Disk, however no data can be copied to a PGP Virtual
Disk.

PGP Virtual Disk

PGP Whole Disk Encryption
•

Any fixed disks that have been encrypted with PGP Desktop using an evaluation
license are automatically decrypted 90 days after the expiration of the evaluation.

Technical Support
Symantec Technical Support maintains support centers globally. Technical Support’s
primary role is to respond to specific queries about product features and functionality.
The Technical Support group also creates content for our online Knowledge Base. The
Technical Support group works collaboratively with the other functional areas within
Symantec to answer your questions in a timely fashion. For example, the Technical
Support group works with Product Engineering and Symantec Security Response to
provide alerting services and virus definition updates.
Symantec’s support offerings include the following:
•

A range of support options that give you the flexibility to select the right amount
of service for any size organization

•

Telephone and/or Web-based support that provides rapid response and
up-to-the-minute information

•

Upgrade assurance that delivers software upgrades

•

Global support purchased on a regional business hours or 24 hours a day, 7 days a
week basis

•

Premium service offerings that include Account Management Services

For information about Symantec’s support offerings, you can visit our Web site at the
following URL:
www.symantec.com/business/support/
All support services will be delivered in accordance with your support agreement and
the then-current enterprise technical support policy.

About PGP Desktop 10.2 for Mac OS X
Technical Support

Contacting Technical Support
Customers with a current support agreement may access Technical Support
information at the following URL:
www.symantec.com/business/support/
Before contacting Technical Support, make sure you have satisfied the system
requirements that are listed in your product documentation. Also, you should be at the
computer on which the problem occurred, in case it is necessary to replicate the
problem.
When you contact Technical Support, please have the following information available:
•

Product release level

•

Hardware information

•

Available memory, disk space, and NIC information

•

Operating system

•

Version and patch level

•

Network topology

•

Router, gateway, and IP address information

•

Problem description:
•

Error messages and log files

•

Troubleshooting that was performed before contacting Symantec

•

Recent software configuration changes and network changes

Licensing and registration
If your Symantec product requires registration or a license key, access our technical
support Web page at the following URL:
www.symantec.com/business/support/

Customer service
Customer service information is available at the following URL:
www.symantec.com/business/support/
Customer Service is available to assist with non-technical questions, such as the
following types of issues:
•

Questions regarding product licensing or serialization

•

Product registration updates, such as address or name changes

•

General product information (features, language availability, local dealers)

•

Latest information about product updates and upgrades

•

Information about upgrade assurance and support contracts

About PGP Desktop 10.2 for Mac OS X
Technical Support

•

Information about the Symantec Buying Programs

•

Advice about Symantec's technical support options

•

Nontechnical presales questions

•

Issues that are related to CD-ROMs or manuals

Support agreement resources
If you want to contact Symantec regarding an existing support agreement, please
contact the support agreement administration team for your region as follows:
Asia-Pacific and Japan

customercare_apac@symantec.com

Europe, Middle-East, Africa

semea@symantec.com

North America, Latin America

supportsolutions@symantec.com

PGP Desktop Basics

This section describes the PGP Desktop terminology and provides some high-level
conceptual information on cryptography.

In This Chapter
PGP Desktop Terminology............................................................................................. 9
Conventional and Public Key Cryptography .............................................................11
Using PGP Desktop for the First Time .......................................................................12

PGP Desktop Terminology
To make the most of PGP Desktop, you should be familiar with the terms in the
following sections.

PGP Product Components
PGP Desktop and its components are described in the following list. Depending on your
license, you may not have all functionality available. For more information, see About
PGP Desktop Licensing (on page 4).
•

PGP Desktop: A software tool that uses cryptography to protect your data against
unauthorized access. PGP Desktop is available for Mac OS X and Windows.
•

PGP Messaging: A feature of PGP Desktop that automatically and
transparently supports all of your email clients through policies you control.
PGP Desktop accomplishes this using a new proxy technology; the older
plug-in technology is also available. PGP Messaging also protects many IM
clients, such as AIM and iChat (both users must have PGP Messaging
enabled).

•

PGP Whole Disk Encryption: Whole Disk Encryption is a feature of PGP
Desktop that encrypts your entire hard drive or partition (on Windows
systems), including your boot record, thus protecting all your files when you
are not using them. You can use PGP Whole Disk Encryption and PGP Virtual
Disk volumes on the same system. On Windows systems, you can protect
whole disk encrypted drives with a passphrase or with a keypair on a USB
token for added security.

•

PGP NetShare: A feature of PGP Desktop for Windows with which you can
securely and transparently share files and folders among selected
individuals. PGP NetShare users can protect their files and folders simply by
placing them within a folder that is designated as protected.

•

PGP Keys: A feature of PGP Desktop that gives you complete control over
both your own PGP keys, and the keys of those persons with whom you are
securely exchanging email messages.

PGP Desktop Basics
PGP Desktop Terminology

•

PGP Virtual Disk volumes: PGP Virtual Disk volumes are a feature of PGP
Desktop that let you use part of your hard drive space as an encrypted
virtual disk. You can protect a PGP Virtual Disk volume with a key or a
passphrase. You can even create additional users for a volume, so that people
you authorize can also access the volume. The PGP Virtual Disk feature is
especially useful on laptops, because if your computer is lost or stolen, the
sensitive data stored on the PGP Virtual Disk is protected against
unauthorized access.

•

PGP Shred: A feature of PGP Desktop that lets you securely delete data from
your system. PGP Shred overwrites files so that even file recovery software
cannot recover them.

•

PGP Viewer: Use PGP Viewer decrypt, verify, and display messages outside
the mail stream

•

PGP Zip: A feature of PGP Desktop that lets you put any combination of files
and folders into a single encrypted, compressed package for convenient
transport or backup. You can encrypt a PGP Zip archive to a PGP key or to a
passphrase.

PGP Universal: A tool for enterprises to automatically and transparently secure
email messaging for their employees. If you are using PGP Desktop in a PGP
Universal Server-managed environment, your messaging policies and other
settings may be controlled by your organization’s PGP administrator.
•

PGP Global Directory: A free, public keyserver hosted by Symantec
Corporation. The PGP Global Directory provides quick and easy access to the
universe of PGP keys. It uses next-generation keyserver technology that
queries the email address on a key (to verify that the owner of the email
address wants their key posted) and lets users manage their own keys. Using
the PGP Global Directory significantly enhances your chances of finding a
valid public key of someone to whom you want to send secured messages.
PGP Desktop is designed to work closely with the PGP Global Directory.

Terms Used in PGP Desktop
Before you use PGP Desktop, you should be familiar with the following terms:
•

Decrypting: The process of taking encrypted (scrambled) data and making it
meaningful again. When you receive data that has been encrypted by someone
using your public key, you use your private key to decrypt the data.

•

Encrypting: The process of scrambling data so that if an unauthorized person gets
access to it, they cannot do anything with it. The data is so scrambled, it’s
meaningless.

•

Signing: The process of applying a digital signature to data using your private key.
Because data signed by your private key can be verified only by your public key,
the ability to verify signed data with your public key proves that your private key
signed the data and thus proves the data is from you.

•

Verifying: The process of proving that the private key was used to digitally sign
data by using that person’s public key. Because data signed by a private key can
only be verified by the corresponding public key, the fact that a particular public
key can verify signed data proves the signer was the holder of the private key.

PGP Desktop Basics
Conventional and Public Key Cryptography

•

Keypair: A private key/public key combination. When you create a PGP “key”, you
are actually creating a keypair. As your keypair includes your name and your
email address, in addition to your private and public keys, it might be more helpful
to think of your keypair as your digital ID—it identifies you in the digital world as
your driver’s license or passport identifies you in the physical world.

•

Private key: The key you keep very, very private. Only your private key can
decrypt data that was encrypted using your public key. Also, only your private key
can create a digital signature that your public key can verify.
Caution: Do not give your private key, or its passphrase, to anyone! And keep
your private key safe.

•

Public key: The key you distribute to others so that they can send protected
messages to you (messages that can only be decrypted by your private key) and so
they can verify your digital signature. Public keys are meant to be widely
distributed.
Your public and private keys are mathematically related, but there’s no way to
figure out your private key if someone has your public key.

•

Keyserver: A repository for keys. Some companies host keyservers for the public
keys of their employees, so other employees can find their public keys and send
them protected messages. The PGP Global Directory (https://keyserver.pgp.com) is
a free, public keyserver hosted by Symantec Corporation.

•

Smart cards and tokens: Smart cards and tokens are portable devices on which
you can create your PGP keypair or copy your PGP keypair. Creating your PGP
keypair on a smart card or token adds security by requiring possession of the
smart card or token in order to encrypt, sign, decrypt, or verify. So even if an
unauthorized person gains access to your computer, your encrypted data is secure
because your PGP keypair is with you on your smart card or token. Copying your
PGP keypair to a smart card or token is a good way to use it away from your main
system, back it up, and distribute your public key. Smart cards and tokens are not
available for key storage when used with PGP Desktop for Mac OS X.

Conventional and Public Key Cryptography
Conventional cryptography uses the same passphrase to encrypt and decrypt data.
Conventional cryptography is great for data that isn’t going anywhere (because it
encrypts and decrypts quickly). However, conventional cryptography is not as well
suited for situations where you need to send encrypted data to someone else, especially
if you want to send encrypted data to someone you have never met.
Public-key cryptography uses two keys (called a keypair) for encrypting and
decrypting. One of these two keys is your private key; and, like the name suggests, you
need to keep it private. Very, very private. The other key is your public key, and, like its
name suggests, you can share it with the general public. In fact, you’re supposed to
share.
Public-key cryptography works this way: let’s say you and your cousin in another city
want to exchange private messages. Both of you have PGP Desktop. First, you both need
to create your keypair: one private key and one public key. Your private key you keep
secret, your public key you send to a public keyserver like the PGP Global Directory
(keyserver.pgp.com), which is a public facility for distributing public keys. (Some
companies have their own private keyservers.)

PGP Desktop Basics
Using PGP Desktop for the First Time

Once the public keys are on the keyserver, you can go back to the keyserver and get
your cousin’s public key, and she can go to the keyserver and get yours (there are other
ways to exchange public keys; for more information, see Working with PGP Keys (on
page 37)). This is important because to send an encrypted email message that only your
cousin can decrypt, you encrypt it using your cousin’s public key. What makes this work
is that only your cousin’s private key can decrypt a message that was encrypted using
her public key. Even you, who have her public key, cannot decrypt the message once it
has been encrypted using her public key. Only the private key can decrypt data that
was encrypted with the corresponding public key.
Your public and private keys are mathematically related, but there’s no feasible way to
figure out someone’s private key if you just have a public key.

Using PGP Desktop for the First Time
Symantec Corporation recommends the following procedure for getting started with
PGP Desktop:
1

Install PGP Desktop on your computer.
If you are a corporate user, your PGP administrator may have specific installation
instructions for you to follow or may have configured your PGP installer with
certain settings. Either way, this is the first step.

Let the Setup Assistant be your guide.
To help you get started, after you install PGP Desktop and reboot your computer,
the Setup Assistant is displayed. It assists with:
•

Licensing PGP Desktop

•

Creating a keypair—with or without subkeys (if you do not already have a
keypair).

•

Publishing your public key on the PGP Global Directory.

•

Enabling PGP Messaging

•

Giving you a quick overview of other features.

If your PGP Desktop installer application was configured by a PGP administrator,
the Setup Assistant may perform other tasks.
3

Exchange public keys with others.
After you have created a keypair, you can begin sending and receiving secure
messages with other PGP Desktop users (once you have exchanged public keys
with them). You can also use the PGP Desktop disk-protection features.
Exchanging public keys with others is an important first step. To send them secure
messages, you need a copy of their public key, and to reply with a secure message,
they need a copy of your public key. If you did not upload your public key to the
PGP Global Directory using the Setup Assistant, do so now. If you do not have the
public key for someone to whom you want to send messages, the PGP Global
Directory is the first place to look. PGP Desktop does this for you—when you send
email, it finds and verifies the keys of other PGP Desktop users automatically. It
then encrypts your message to the recipient public key, and sends the message.

Validate the public keys you get from untrusted keyservers.

PGP Desktop Basics
Using PGP Desktop for the First Time

When you get a public key from an untrusted keyserver, try to make sure that it
has not been tampered with, and that the key really belongs to the person it
names. To do this, use PGP Desktop to compare the unique fingerprint on your
copy of someone’s public key to the fingerprint on that person’s key (a good way to
do that is by telephoning the key’s owner and having them read you the
fingerprint information so that you can compare it). Keys from trusted keyservers
like the PGP Global Directory have already been verified.
5

Start securing your email, files, and instant message (IM) sessions.
After you have generated your keypair and exchanged public keys, you can begin
encrypting, decrypting, signing, and verifying email messages and files. The
secure IM chat session feature generates its own keys automatically, so you can
use this feature even before you generate your keypair. The only requirement is
that you must be chatting with another PGP Desktop user for the chat session to
be secured.

Watch for information boxes from the PGP Desktop Notifier feature to appear.
As you send or receive messages, or perform other PGP Desktop functions, the
PGP Desktop Notifier feature displays information boxes that appear in whichever
corner of the screen you specify. These PGP Notifier boxes tell you the action that
PGP Desktop took, or will take. After you grow familiar with the process of sending
and receiving messages, you can change options for the PGP Notifier feature—or
turn it off.

After you have sent or received some messages, check the logs to make sure
everything is working correctly.
If you want more information than the Notifier feature displays, the PGP Log
provides detailed information about all messaging operations.

Modify your messaging policies, if necessary.
Email messages are sent and received—automatically and seamlessly—if PGP
Desktop messaging policies are configured correctly. If your message recipient has
a key on the PGP Global Directory the default PGP Desktop policies provide
opportunistic encryption. Opportunistic encryption means that, if PGP Desktop
has what it needs (such as the recipient's verified public key) to encrypt the
message automatically, then it does so. Otherwise, it sends the message in clear
text (unencrypted). The default PGP Desktop policies also provide optional forced
encryption. This means that, if you include the text “[PGP]” in the Subject line of a
message, then the message must be sent securely. If verified keys cannot be found,
then the message is not sent, and a Notifier box alerts you.

Start using the other features in PGP Desktop.
Along with its messaging features, you can also use PGP Desktop to secure the
disks that you work with:
•

Use PGP Whole Disk Encryption to encrypt a boot disk, disk partition (on
Windows systems), external disk, or USB thumb drive. All files on the disk or
partition are secured — encrypted and decrypted on the fly as you use them.
The process is completely transparent to you.

•

Use PGP Virtual Disk to create a secure “virtual hard disk.” You can use this
virtual disk like a bank vault for your files. Use PGP Desktop or Windows
Explorer or the Mac OS X finder to unmount and lock the virtual disk, and
your files are secure, even if the rest of your computer is unlocked.

•

Use PGP Zip to create compressed and encrypted PGP Zip archives. These
archives offer an efficient way to transport or store files securely.

PGP Desktop Basics
Using PGP Desktop for the First Time

•

Use PGP Shredder to delete sensitive files that you no longer need. PGP
Shredder removes them completely, eliminating any possibility of recovery.

Installing PGP Desktop

This section describes how to install PGP Desktop onto your computer and how to get
started after installation.

In This Chapter
System Requirements...................................................................................................15
Installing and Configuring PGP Desktop...................................................................15
Uninstalling PGP Desktop ...........................................................................................20
Moving Your PGP Desktop Installation from One Computer to Another ............21

System Requirements
The minimum system requirements to install PGP Desktop on your Mac OS X system
are:
•

Apple Mac OS X10.5.x or 10.6.x (Intel)

•

512 MB of RAM

•

64 MB hard disk space

•

PGP Whole Disk Encryption (PGP WDE) is not compatible with any third-party
software, other than Apple Boot Camp, that could bypass the PGP WDE protection
on the Master Boot Record (MBR) and write to or modify the MBR. Boot Camp
needs to modify MBR before installing the Windows OS and cannot be used on a
Macintosh system that is already encrypted with PGP WDE. To use Boot Camp
with PGP WDE, refer to the installation instructions in the PGP Desktop for Mac
OS X User's Guide.

PGP Whole Disk Encryption (PGP WDE) is not compatible with any third-party
software, other than Apple Boot Camp, that could bypass the PGP WDE protection on
the Master Boot Record (MBR) and write to or modify the MBR. Boot Camp needs to
modify MBR before installing the Windows OS and cannot be used on a Macintosh
system that is already encrypted with PGP WDE. To use Boot Camp with PGP WDE,
refer to the installation instructions.

Installing and Configuring PGP Desktop
This section includes information on installing or upgrading PGP Desktop, as well as
information on the Setup Assistant.

Installing PGP Desktop
Installing and Configuring PGP Desktop

Installing the Software
Note: You must have administrative rights on your system in order to install the
update.
The PGP Desktop installer walks you through the installation process.
To install PGP Desktop on your Mac OS X system
1

Quit all other applications.

Mount the PGP DiskCopy image.

Double-click PGP.pkg.

Follow the on-screen instructions.

If prompted to do so, restart your system.
Note: If you are in a domain protected by a PGP Universal Server, your PGP
administrator may have preconfigured your PGP Desktop installer with specific
features and/or settings. In addition, if your PGP administrator set up silent
enrollment, your Windows domain password will be used for all passphrase
requirements in PGP Desktop. If specified by policy, PGP Whole Disk Encryption may
automatically start to encrypt your disk when your Windows password is entered.

Using PGP Desktop with Apple Boot Camp
Apple Boot Camp is compatible with PGP Desktop ver 10.0 or later. To use PGP Desktop
with Boot Camp, you must install the software and encrypt the disk in a specific order.
Before you begin, be sure you have installed Boot Camp correctly. For information on
how to set up Boot Camp, refer to the Boot Camp Installation and Setup Guide
(http://manuals.info.apple.com/en/boot_camp_install-setup.pdf) from Apple. Note that
in order to use Windows XP in the Windows partition, you much configure the partition
as FAT32. PGP Desktop does not support installing Linux on a partition in Boot Camp.
If you need to decrypt your disk, Symantec Corporation recommends that you do so
from the Mac OS X partition.
For more information on using PGP Desktop with Apple Boot Camp, see PGP KB Article
1697 (https://support.pgp.com/?faq=1697).
Note: Be sure that your disk is not encrypted (if it is, decrypt the disk before
installing Boot Camp) and then uninstall PGP Desktop.
To use Apple Boot Camp in a standalone environment
1

Install Apple Boot Camp.

Install PGP Desktop on the Mac OS X partition and complete installation with the
setup assistant.

Boot into the Windows partition and install PGP Desktop on the Windows. Do not
run the setup assistant on the Windows partition.

Installing PGP Desktop
Installing and Configuring PGP Desktop

Boot into the Mac OS X partition and encrypt your disk. At this point, if you pause
the encryption process while running Mac OS X, you can boot into the Windows
partition but you must resume encryption while running Mac OS X.

To use Apple Boot Camp in a PGP Universal Server-managed environment
1

Install Apple Boot Camp.

Boot into the Windows partition and install PGP Desktop on the Windows. Do not
run the setup assistant on the Windows partition.

Install PGP Desktop on the Mac OS X partition and complete enrollment with the
setup assistant.

While still booted into the Mac OS X partition, begin to encrypt your disk. At this
point, if you pause the encryption process while running Mac OS X, you can boot
into the Windows partition but you must resume encryption while running Mac
OS X.

Upgrading the Software
Note: PGP Desktop for Mac OS X, and PGP Universal Satellite for Mac OS X cannot
both be installed in the same system. The installers for both products will detect the
presence of the other program and end the install.
You can upgrade to PGP Desktop for Mac OS X from a previous version of one of the
following products:
•

PGP Desktop for Mac OS X

•

PGP Universal Satellite for Mac OS X
Important Note: If you are upgrading your computer to a new version of the
operating system and want to use this version of PGP Desktop, be sure to uninstall
any previous versions of PGP Desktop before upgrading the OS and installing this
release. Be sure to back up your keys and keyrings before uninstalling. Note that if
you have used PGP Whole Disk Encryption, you will need to unencrypt your disk
before you can uninstall PGP Desktop.

Upgrading PGP Desktop
Tip: When upgrading PGP Desktop on a Mac OS X 10.6 system, you are prompted to
allow various PGP components (such as the PGP Engine) to access information in
your keychain. This prompt can appear several times as there are several
components that require access to the keychain. To avoid seeing this prompt more
than once, be sure to select Always Allow.
Do one of the following:
•

From PGP Desktop 8.x or 9.x for Mac OS X, begin the installation process for PGP
Desktop 10.2 for Mac OS X.
The existing version of PGP Desktop for Mac OS X is automatically uninstalled,
then PGP Desktop 10.2 for Mac OS X is installed. Existing keyrings and PGP
Virtual Disk files are usable in the upgraded version.

Installing PGP Desktop
Installing and Configuring PGP Desktop

•

From a version of PGP Desktop for Mac OS X prior to Version 8.0, you must
manually uninstall the existing software before beginning the installation of PGP
Desktop 10.2 for Mac OS X. Existing keyrings and PGP Virtual Disk files are usable
in the upgraded version.

Upgrading from PGP Universal Satellite
Do one of the following:
•

From PGP Universal Satellite version 1.2 or previous for Mac OS X, begin the
installation process for PGP Desktop 10.2 for Mac OS X.
Existing versions of PGP Universal Satellite for Mac OS X are automatically
uninstalled, then PGP Desktop 10.2 for Mac OS X is installed. Existing settings are
retained.
Caution: Installing any version of PGP Universal Satellite on top of PGP Desktop
10.2 for Mac OS X is an unsupported configuration. Neither program will work
correctly. Uninstall both programs and then reinstall only PGP Desktop.

•

From PGP Desktop for Mac OS X (version 8.x) and PGP Universal Satellite:
Follow the installation process for PGP Desktop 10.2 for Mac OS X.
PGP Desktop for Mac OS X and PGP Universal Satellite for Mac OS X are both
automatically uninstalled, then PGP Desktop 10.2 for Mac OS X is installed.
Existing keyrings and PGP Virtual Disk files are usable in the upgraded version, as
are existing PGP Universal Satellite for Mac OS X settings.

Upgrading PGP Desktop with Apple Boot Camp Installed
In order to upgrade PGP Desktop for Mac OS X to 10.2, you must use the following
procedure:
1

Use Apple Boot Camp and boot into Windows.

Upgrade PGP Desktop (in the Windows partition).

Reboot into Mac OS X.

Upgrade PGP Desktop (in the Mac OS X partition).

Reboot into Mac OS X and allow the PGP BootGuard upgrade to occur.

Reboot into Mac OS X again to verify the PGP Bootguard upgrade is successful.

Reboot into Windows to verify Bootguard is upgraded and you can log on to
Windows.

Checking for Updates
Note: The option to automatically check for updates is no longer available in PGP
Desktop, starting with version 10.1. To check for an update or to install an update,
you must manually download the file.

Installing PGP Desktop
Installing and Configuring PGP Desktop

With the acquisition of PGP Corporation by Symantec Corporation, PGP operations is in
the process of integrating with Symantec operations. When checking to see if there are
updates, or to download an update, use the second download link if the first link does
not appear operational.
To upgrade PGP Desktop, do the following:
•

Go to the PGP License and Entitlement Management System (LEMS) and log in
(https://lems.pgp.com/account/login). If the update for PGP Desktop is not
available, then

•

Go to Symantec FileConnect (https://fileconnect.symantec.com/), select your
language, and enter your serial number.

Upgrading From Standalone to Managed PGP Desktop Installations
If you have been using PGP Desktop in standalone mode and now will be managed by a
PGP Universal Server, you must install a bound and stamped version of PGP Desktop
over your existing, standalone installation. You must also complete the enrollment
process. Your PGP Administrator will provide an installation file so you can install a
bound and stamped version.

Upgrading the Operating System Software
If you are upgrading your computer to a new major release of the operating system (for
example, on a Windows system to Windows Vista or on a Mac OS X system from 10.4.x
to 10.5.x), be sure to do the following:
1

Back up your keys and keyrings before uninstalling.

If you have used PGP Whole Disk Encryption, decrypt your disk before you
uninstall PGP Desktop.

Uninstall any previous versions of PGP Desktop before upgrading to the new
version of the operating system.

Once you have upgraded your version of the operating system, reinstall PGP
Desktop. Import your keys/keyring and, if necessary, you can then encrypt your
disk.

Licensing PGP Desktop
For license information for this release, see the PGP Desktop Release Notes.

Running the Setup Assistant
The Setup Assistant displays a series of screens that ask you questions—then uses your
answers to configure PGP Desktop for you.
If you have questions about any of the content on the Setup Assistant screens, click
Help on the screen.

Installing PGP Desktop
Uninstalling PGP Desktop

The Setup Assistant does not configure all PGP Desktop settings. When you finish
going through the Setup Assistant screens, you can then configure those settings not
covered in the Setup Assistant.

Integrating with Entourage 2008
The PGP Desktop for Mac OS X installation package includes scripts so you can
integrate PGP Desktop with Entourage. Once the scripts are copied to the required
folders, the Scripts menu in Entourage includes a PGP menu option. Use the Entourage
scripts to encrypt email text without having to use an email proxy.
To integrate PGP scripts with Entourage
1

If it is running, quit Entourage.

Open the PGP Desktop for Mac OS X download.

In the PGP Desktop download folder, open the Extras folder.

In the Extras folder, open the Entourage folder.

Double-click the file EntourageScripts.zip to extract the following scripts
from the zip file:

•

Decrypt & Verify\mod

•

Encrypt & Sign\moc

•

Encript\moe

•

Sign\mos

Copy and paste the scripts to the following folder:
•

User Profile\Documents\Microsoft User Data\Entourage Script Menu
items\PGP

Start Entourage. The Scripts menu now includes a PGP menu option.

See Using PGP Scripts with Entourage 2008 (on page 104) for information on how to
encrypt and decrypt messages.

Uninstalling PGP Desktop
To uninstall PGP Desktop
1

In PGP Desktop, from the PGP menu, select Uninstall. A confirmation dialog box
is displayed.

Click Yes to continue with the uninstall process.

You are prompted to authenticate as the administrative user of the Mac OS X
system from which you are uninstalling PGP Desktop. Enter the appropriate
password, then click OK. The PGP Desktop software is removed from your system.

Your keyring and PGP Virtual Disk files are not removed from your system, in case you
decide to reinstall PGP Desktop in the future.

Installing PGP Desktop
Moving Your PGP Desktop Installation from One Computer to Another

Moving Your PGP Desktop Installation from One Computer
to Another
Moving a PGP Desktop installation from one computer to another is not a difficult
process, although there are a few crucial steps which must be completed successfully.
The process consists of the following steps:
To transfer your PGP Desktop installation to another computer
1

Uninstall PGP Desktop. To do this, in PGP Desktop from the PGP menu, select
Uninstall.
Note that this step does not remove the keyring files.

Transfer the keyrings. To do this, copy the keyring files (both pubring.pkr and
secring.skr) from the old computer to removable media such as a flash drive,
and then copy them to the new computer. The default location for the keyring files
is in the PGP folder.
If PGP Desktop has never been installed on the new computer, create this folder
first before copying the keyring files to the computer.

Install PGP Desktop on the new computer. To do this, download PGP Desktop by
clicking the download link in your original PGP order confirmation email.

During the installation process, do the following:
•

During the PGP Desktop setup wizard on the new computer select No, I have
existing keyrings and specify the location where you copied the keyring files
to on the new computer.

•

Use the same name, organization, and license number used when PGP
Desktop was originally authorized.

The PGP Desktop User Interface

This section describes the PGP Desktop user interface.

In This Chapter
Accessing PGP Desktop Features................................................................................23
PGP Desktop Notifier alerts.........................................................................................27
PGP Desktop and the Finder........................................................................................31
Viewing the PGP Log.....................................................................................................36

Accessing PGP Desktop Features
There are four main ways to access PGP Desktop:
•

PGP Desktop Main Screen (on page 24)

•

Using the PGP Desktop Icon in the Menu Bar (on page 25)

•

Using the PGP Dock Icon (on page 26)

•

Using the Mac OS X Finder (on page 27)

The PGP Desktop User Interface
Accessing PGP Desktop Features

PGP Desktop Main Screen
The main screen of PGP Desktop is your primary interface to the product.

The PGP Desktop main screen includes:
1

The search field. Lets you search for keys on the local keyring.
Simply enter characters and the names and email addresses on the
local keyring that include those characters will display. Click
Advanced Search for more search criteria.

The PGP Desktop Work area. Displays information about and
actions you can take for the selected item.

The Toolbar. Provides access to frequently used features. You can:
Create a new PGP Zip archive.
Create a new PGP Virtual Disk.
Mount an existing PGP Virtual Disk.
Synchronize keys.
Shred files.

The Keys item. Gives you control over the PGP keys that PGP
Desktop is managing for you.

The PGP Disk item. Use this item to view and manage PGP Virtual
Disk volumes. Also, you can use this item to create new PGP Virtual
Disk volumes, as well as encrypting an entire non-boot disk using the
PGP Whole Disk Encryption feature.

The PGP Messaging item. Use this item to manage PGP
Messaging services. You can also use this item to create new services
and policies, and manage existing services and policies.

The Keyservers item. Use this item to view and manage
keyservers.

The PGP Desktop User Interface
Accessing PGP Desktop Features

( not shown) The PGP Zip item. Use this item to view and manage
PGP Zip archives.

Using the PGP Desktop Icon in the Menu Bar
One way to access many PGP Desktop features is from the PGP Desktop icon in the
Menu Bar.

When you click the PGP Desktop icon in the Menu Bar, the PGP menu is displayed. Note
that not all options may be available, depending on if you are a standalone or managed
installation.
•

About PGP Desktop. Displays a window with information about the version of
PGP Desktop you are using, licensing information, and a list of the people who
helped create PGP Desktop. This window also has a button that you can use to
uninstall PGP Desktop.

•

Help. Opens the PGP Desktop integrated online help.

•

Open PGP Desktop. Opens the PGP Desktop main screen.

•

Open PGP Viewer. Opens PGP Viewer so you can decrypt email out of the mail
stream.

•

View Notifier. Displays the PGP Desktop Notifier box, so you can review the
Notifier messages that have appeared.

•

Show Log. Displays the PGP Desktop Log. Use the PGP Desktop Log to see what
actions PGP Desktop is taking to secure your data.

•

Clear Log. Clears the PGP Log.

•

Update Policy. Manually downloads policy from the PGP Universal Server. This
option is available only for managed installations.

•

Change Passphrase. Provides a shortcut so you can change your passphrase on
your key. This option is available only for managed installations.

•

Purge Caches. Clears from memory any cached information, such as passphrases
and cached public keys.

•

Hide. Removes the PGP icon from the menu bar, but leaves the background parts
of the application running.
The Hide command becomes the Quit command if you hold down the Option key
before clicking the PGP Desktop icon. This removes the PGP Desktop icon from the
menu bar and causes the background parts of PGP Desktop to quit. Shortcut menu
functionality continues to work.

The PGP Desktop User Interface
Accessing PGP Desktop Features

Caution: If you use the Option key and the PGP Menu Bar icon to quit the
background parts of PGP Desktop, email messages are no longer encrypted,
decrypted, signed, or verified. You may also not be able to decrypt messages
received while the background parts of PGP Desktop were not running, even
after they are started again. Finally, no key management is done while the
background parts of the software is not running. For these reasons, it is
recommended that you keep the PGP Desktop background processes running at
all times.
To restart the background processes of PGP Desktop if the application is not running
1

Locate the PGP Desktop application on your system. The default location is in the
Applications folder.

Double-click the PGP Desktop application icon. PGP Desktop starts and its icon is
displayed in the Menu Bar.

Using the PGP Dock Icon
One way to access many PGP Desktop features is from the PGP Dock icon.

Use the PGP Desktop icon in the Mac OS X Dock in any of these ways, then select an
option from the menu displayed:
•

Click the PGP Desktop Dock icon and hold the mouse button down.

•

Ctrl+click the Dock icon.

•

Right-click the Dock icon, if you are using a two-button mouse.

The PGP Desktop icon is displayed in the Dock when the application is open, or when
you have put the PGP Desktop icon into the Dock manually.
When you click and hold the PGP Desktop icon in the Dock when the application is
already open (or Ctrl+click it, or use the right mouse button if you are using a
two-button mouse), a menu is displayed giving you access to the following commands:
•

Any currently-open PGP Desktop windows. If PGP Desktop is currently running,
any of its windows that you have open appear at the top of this menu.

•

About PGP Desktop. Displays the PGP Desktop About dialog box. The About
dialog box displays the PGP Desktop credits, what version you are currently using,
and has a button that you can use to uninstall the PGP Desktop software.

•

Preferences. Opens the PGP Desktop Preferences.

•

Clipboard. Lets you Encrypt, Sign, Encrypt & Sign, or Decrypt/Verify the contents
of the Clipboard.

•

Purge Caches. Clears from memory any cached information, such as passphrases
and cached public keys.

The remaining menu items, in the lowest section of the menu, are standard Mac OS X
Dock items:

The PGP Desktop User Interface
PGP Desktop Notifier alerts

•

Remove from Dock/Keep in Dock. Removes or adds the PGP Desktop icon in the
Dock.

•

Open at Login. Sets your Mac OS X Account System Preference so that PGP
Desktop starts when you log on to your computer.

•

Show In Finder. Shows the location of the PGP Desktop application in a Finder
window.

•

Hide. Hides any PGP Desktop application screens.

•

Quit. Quits the PGP Desktop application.

If you click and hold the PGP Desktop icon in the Dock when the application is not open,
you see the standard Mac OS X Dock items.

Using the Mac OS X Finder
From the Desktop or a Finder window, Ctrl+click a file or folder (or right-click it if you
have two-button mouse) then select PGP from the shortcut menu displayed.
You can also access PGP Desktop functions from the Mac OS X Finder.
To use the Mac OS X Finder
1

Open a Finder window.

Ctrl+click (or right-click, if you are using a two-button mouse) the desired file or
folder.

Select the appropriate option from the PGP shortcut menu. Choose Encrypt, Sign,
Encrypt & Sign, Decrypt/Verify, Shred, or Mount (if you have PGP Virtual Disks).
Tip: You can also right-click a file or folder from the Desktop.

PGP Desktop Notifier alerts
The PGP Desktop Notifier feature displays a small information box that tells you the
status of incoming and outgoing email messages, as well as instant messaging sessions.
In a PGP Universal Server-managed environment, your administrator may have
specified certain notifications settings (for example, whether notifications are to be
displayed or the location of the notifier). In this case, you may not see any notifier
messages at all.

PGP Desktop Notifier for Messaging
Use the PGP Desktop Notifier for Messaging feature to:
•

See if an incoming email is properly decrypted and/or signed.

•

See if an outgoing email is properly encrypted and/or signed.

The PGP Desktop User Interface
PGP Desktop Notifier alerts

•

Stop an email message from being sent if the encryption options are not what you
want.

•

View a quick summary of the sender, subject, and encryption key of an email.

•

Review, at any time, the status of previous incoming or outgoing messages for that
Windows session.

•

See that a chat session with another PGP Desktop user is being secured.

Use the PGP Desktop Notifier feature to monitor all or some of your incoming email, as
well as maintain precise control over all or some of your outgoing messages. The choice
is yours. You can set various Notifier options, or turn the PGP Desktop Notifier feature
completely off if you prefer.
Some additional points about the PGP Desktop Notifier feature:
•

For message notifications, use the left and right arrow buttons in the upper-right
corner of the Notifier box to scroll Notifier messages forward or backward. This
way, you can review messages that came before or after the message you are
viewing currently.

•

When they first display, Notifier message boxes have a partially transparent
appearance to prevent obscuring anything on your screen. Notifier message boxes
become opaque if you move your cursor over them, and become translucent again
when you move your cursor away from them.

•

Unless the cursor is over them, Notifier messages display for four seconds (this
default setting can be changed in the Notifier options). If you want more time to
read a Notifier, move your cursor over the Notifier and it remains on your display.

•

If you completely miss reading a Notifier, or you would like to review previous
ones, do the following:

•

On Windows systems, choose View Notifier from the PGP Tray icon.

•

On Mac OS X systems, choose View Notifier from the PGP Desktop icon in
the Mac OS X Menu Bar.

Close a Notifier message by clicking the X (in the upper right corner of the
message on Windows systems, in the upper left corner on Mac OS X systems).

For more information about setting PGP Desktop Notifier options, see Notifier Options
(see "Notifications Preferences" on page 174).

Incoming PGP Desktop Notifier messages
Notifications for incoming email provide information on whether the email was
decrypted and verified, or decrypted and signed by an unverified or unknown key.

Outgoing PGP Desktop Notifier messages
For simple notification, choose to have a PGP Desktop Notifier appear momentarily
when email is sent (all email, or email meeting certain criteria). The notifier message
displays information that PGP Desktop is searching for the public keys of the person in
the To line. When the appropriate keys are found, the Status line changes to indicate
the message will be sent encrypted. If the appropriate keys cannot be found, PGP
Desktop follows policy and may send the message unencrypted or block the message.

The PGP Desktop User Interface
PGP Desktop Notifier alerts

After a message has been sent encrypted, click More to see the details of how PGP
Desktop handled the message. It is not necessary for you to view this additional
information unless you want to see it. To hide the additional information again, click
Less.
You can delay a message from being sent by moving your cursor over the Notifier box.
If you do not do this within 4 seconds (you can set this interval in preferences for the
Notifier feature) the message is sent unencrypted, and the Status field reflects that.
If you do move your cursor over the message, Block and Send buttons appear in the
Notifier box. Click Block to stop the message from being transmitted, or Send to send
the message.
If you send an email to more than one recipient, and PGP Desktop is able to find keys
for some recipients but not others, the Notifier informs you of the status, and gives you
two options:
•

Send the email encrypted to those with keys, and unencrypted to those without
them.

•

Block the message so it is sent to no one.

Outgoing PGP Desktop Notifier Messages for Offline Policy
If you are using PGP Desktop in a PGP Universal Server-managed environment, your
administrator may have specified what actions to take on outgoing messages if the PGP
Universal Server is not available. The outgoing notifier message indicates one of the
following:
•

Your PGP Universal Server is not available and policy has been set to block all
messages. Email messages remain in your outbox and are sent when the PGP
Universal Server can be contacted.

•

Your PGP Universal Server is not available and policy has been set to send all
messages in the clear.

•

Your PGP Universal Server is not available and policy has been set to allow your
local policy to take precedence.

In the latter two cases, you can choose to send or block the outgoing message as you
would any other outgoing message.

PGP Notifier for Instant Messaging
If you have PGP Desktop installed on your computer, and if you have specified to
receive Notifiers for Instant Messaging (under the Notifications tab in PGP Desktop
Preferences), then PGP Desktop Notifiers alert you when the AOL Instant Messenger
(AIM) sessions that you have with other PGP Desktop users are protected.
When you use the secure instant messaging feature, a Notifier displays when you log on
to the instant messaging program to inform you that your chat is secure, and a padlock
icon displays next to your “buddy name” with most AIM-compliant instant messaging
clients.
When you log off of your instant messaging program, a final Notifier message informs
you that the secure session has ended.
For more information on proper configuration, as well as the use of the secure instant
message chat feature, see Securing Instant Messages.

The PGP Desktop User Interface
PGP Desktop Notifier alerts

Enabling or Disabling Notifers
In a PGP Universal Server-managed environment, your administrator may have
specified certain notifications settings (for example, whether notifications are to be
displayed or the location of the notifier). In this case, the Notifications Preferences
panel is not available and not displayed.
To enable or disable Notifiers
1

Open PGP Desktop and select PGP > Preferences.

Click the Notifier icon.

Under Usage, specify if you want to Use PGP Notifer and, if so, the location. PGP
Desktop Notifications can appear at any of the four corners of your screen (Lower
Right, Lower Left, Upper Right, or Upper Left). Select the corner that you want
PGP Desktop Notifications to appear. The default position is Upper Left.

If you are using PGP Desktop Messaging and you want PGP Desktop Notifiers to
appear, informing you of encryption and/or signing status when you send email,
select the checkbox to Notify when processing outbound email. Deselect this
checkbox to stop PGP Desktop Notifiers from appearing when you send mail.

PGP Desktop looks for a public key for every recipient of the email messages that
you send. By default, if it cannot find a public key for a recipient, it sends that
email in the clear (without encryption). Select Ask me before sending email when
the recipient’s key is not found if you want to be notified when a key is not found
and be given a chance to block the email so that it is not sent. Then specify the
following options:
•

Always ask me before sending email: Select this checkbox if you would
prefer approving every email that you send. You can review the encryption
status in the Notifier, and either send or block the email.

•

Delay outbound email for n second(s) to confirm (where n is a number from
1-30; the default is 4 seconds). To change the amount of time that outbound
messages are delayed, and a PGP Desktop Notifier is displayed, click the up
or down arrows. Use the delay period to review the PGP Desktop Notifier
message.

(For more information on the PGP Desktop default policy settings, see Services and
Policies (on page 79).)
6

For incoming email, specify how you are notified of its status upon arrival. Select
one of the following for Display notifications for incoming mail:
•

When receiving secured email—A Notifier appears whenever you receive
secured email. The box displays who the email is from, its subject, its
encryption and verification status, and the email address of the person
sending it.

•

Only when message verification fails—For incoming email, you see a
Notifier only when PGP Desktop is unable to verify the signature of the
incoming email.

•

Never—If you do not need or want to see a Notifier as you receive email,
select this option. This option does not affect Notifiers for outgoing mail.

If you want a PGP Desktop Notifier to appear briefly when you begin a secure
instant message chat, and appear briefly again when the chat ends, select the
checkbox to Notify for status of PGP Encrypted IM sessions.

The PGP Desktop User Interface
PGP Desktop and the Finder

PGP Desktop and the Finder
This section describes how you can access certain PGP Desktop functions using
shortcut menus in the Finder.

Overview
Access PGP Desktop functions using shortcut menus in the Finder to get the same PGP
Desktop functionality from the Mac OS X Services menu.
Depending on what you select, you can:
•

Encrypt, Sign, or Encrypt and Sign

•

Shred

•

Decrypt/verify

•

Mount, edit, or unmount a PGP Virtual Disk volume

•

Import a PGP key

•

Add PGP keys to your keyring

View the contents of a PGP Zip archive Access shortcut menus in the Finder by:
•

Ctrl+clicking: With a one-button mouse, hold down the Control (ctrl) key on the
keyboard and click the item.

•

Right-clicking: On a two-button mouse, click the item with the right mouse button
held down.
Tip: In Mac OS X 10.6, Apple changed the way shortcuts are available from the
Finder. In order to enable shortcuts to encrypt or sign files, or mount disks, you must
first enable the keyboard shortcuts in the Services preferences. To do this, open
System Preferences and open the Keyboard option. Select the Keyboard Shortcuts
panel and verify the PGP shortcuts are there. Then, to perform any encrypt or sign
functions, select the file, choose Finder > Services, and select the appropriate option.

In this document, the Ctrl+click method is used. If you right-click or use a different
method for accessing shortcut menus in the Finder, substitute that method where it
says to Ctrl+click.
Note: Files “in the Finder” also include files on the Mac OS X Desktop.

Encrypt, Sign, or Encrypt and Sign
PGP Desktop lets you encrypt, sign, or encrypt and sign unencrypted files, folders, and
even entire drives from the Finder.
Encrypting and/or signing files and folders is a good way to protect just a few important
files and/or folders in a situation where a PGP Virtual Disk volume is not justified.

The PGP Desktop User Interface
PGP Desktop and the Finder

If you are considering encrypting and/or signing a drive in the Finder, a PGP Virtual
Disk volume might be a better solution. For more information, see Using PGP Virtual
Disks.
To encrypt and/or sign files and/or folders in the Finder
1

In the Finder, select the files and/or folders you want to encrypt and/or sign. Use
the Shift or Command keys to select any combination of files and folders.

Ctrl+click the selected files and/or folders, or right-click if you have a two-button
mouse. From the shortcut menu, choose Encrypt & Sign from the PGP menu. (If
you select just Encrypt, you will not be prompted for a signing key; if you select
just Sign, you will not be prompted to select a public key to encrypt to.) The PGP
Recipients dialog box is displayed.

Drag the public keys of the persons you want to be able to decrypt the items you
are encrypting into the Recipients field at the bottom of the dialog box.

Click the down arrow icon above the OK button to specify the appropriate options:
•

Conventional Encrypt. Select this checkbox to rely on a common passphrase
rather than on public-key cryptography. The file is encrypted using a session
key, which encrypts (and decrypts) using a passphrase you specify.
If you are using PGP Desktop in a PGP Universal Server-managed environment,
conventional encryption may be disabled.

•

Text Output. When sending files as attachments with some email
applications, you may need to select the Text Output checkbox to save the
file as ASCII text. This is sometimes necessary in order to send a binary file
using older email applications. Selecting this option increases the size of the
encrypted file by about 30 percent.

•

Shred Original. Select this checkbox to overwrite the original document that
you are encrypting, so that your sensitive information is not readable by
anyone who can access your system.

•

MacBinary. MacBinary is the standard method by which a Mac OS X file is
converted into a single file so that it can be transferred to another Macintosh
or PC without losing either its Data or Resource segment. Options are Yes,
No, or Smart.
Yes means the whole file is included, including the Mac OS X specific
information. No means only the data segment is included. Smart means the
file type determines if the Mac OS X specific information is included.

Click OK. If you selected the Conventional Encryption option, you are prompted
for a passphrase to protect the encrypted items.

Enter a passphrase, enter it again, then click OK. The Enter PGP Passphrase dialog
box is displayed.

Using the Signing Key list, specify a private key to be used to sign the items you
are encrypting and signing, then enter the passphrase of the signing key. If the
passphrase is cached, you do not have to enter it.
Normally, as an added level of security, the characters you enter for the
passphrase do not appear on the screen. However, if you are sure that no one is
watching (either physically or over the network) and you would like to see the
characters of your passphrase as you type, select the Show Keystrokes checkbox.

To save your passphrase in the Mac OS X Keychain, select the box. You will not
need to enter the passphrase the next time you access this feature.

The PGP Desktop User Interface
PGP Desktop and the Finder

Click OK. A PGP Zip archive (.pgp) file is created at the same location
as the encrypted and signed items.

Shred
For those situations where you want to be absolutely certain that specific files and/or
folders are securely deleted from your system, you can Shred them from the Finder.
Putting a file or folder into the Mac OS X Trash just allows new files to overwrite the file
or folder you think you are “deleting.” In fact, there could be days, weeks, or even
months when just about anyone with physical access your system could retrieve these
files.
The PGP Desktop Shred feature, in comparison, overwrites your files multiple times as
soon as you ask them to be shredded. For more information about how thoroughly the
Shred feature erases your files, see Shredding Files.
To Shred files and/or folders in the Finder
1

In the Finder, select the files and/or folders you want to Shred. Use the Shift or
Command keys to select any combination of files and folders.

Ctrl+click the selected files and/or folders, or right-click if you are using a
two-button mouse.

Choose PGP, then Shred from the shortcut menu. A PGP screen is displayed,
asking if you are sure you want to Shred the listed files.

Click OK. The file(s) are Shredded (secure deleted) from your system; they do not
appear in the Trash.

Decrypt/Verify
If you have a PGP Zip (.pgp) file on your system, you can decrypt and verify it in the
Finder. Decrypt/verify will always decrypt an encrypted (.pgp) file. However, if the
encrypted file was not signed, then the file will not be verified (as there’s no signature
to verify).
You can also decrypt/verify a PGP key (.asc) file, but this is just for importing the keys,
not for decrypting or verifying the file. For more information about importing PGP keys
from a .asc file in the Finder, see Import a PGP Key (on page 34).
To decrypt/verify a PGP Zip file in the Finder
1

In the Finder, select the PGP Zip (.pgp) file you want to decrypt/verify.

Ctrl+click the selected files and/or folders, or right-click if you are using a
two-button mouse. Choose PGP, then Decrypt & Verify from the shortcut menu.
The Enter PGP Passphrase dialog box is displayed.

Enter the appropriate passphrase for the private key. If the passphrase is cached,
you aren’t prompted for it.

The PGP Desktop User Interface
PGP Desktop and the Finder

Normally, as an added level of security, the characters you enter for the
passphrase do not appear on the screen. However, if you are sure that no one is
watching (either physically or over the network) and you would like to see the
characters of your passphrase as you type, select the Show Keystrokes checkbox.
4

To save your passphrase in the Mac OS X Keychain, select the box. You will not
need to enter the passphrase the next time you access this feature.

Click OK. The file is decrypted at the location of the .pgp file. If the file was
signed, PGP Desktop opens the Verification Info window and displays the results
of the verification of the file.

Mount or Unmount a PGP Virtual Disk Volume
If you have an unmounted PGP Virtual Disk (.pgd) file, you can mount the
corresponding PGP Virtual Disk volume from the Finder. For more information about
PGP Virtual Disk volumes, see Using PGP Virtual Disks.
To mount a PGP Virtual Disk volume from the Finder
1

In the Finder select the PGP Disk (.pgd) file for the volume you want to mount.
Ctrl+click the selected .pgd file, or right-click if you are using a two button
mouse. From the PGP menu, select Mount. The Enter PGP Passphrase dialog box
is displayed.

Enter the passphrase that protects the PGP Disk volume you want to mount.
Normally, as an added level of security, the characters you enter for the
passphrase do not appear on the screen. However, if you are sure that no one is
watching (either physically or over the network) and you would like to see the
characters of your passphrase as you type, click Typing Hidden.

Click OK. The PGP Disk volume is mounted.

To unmount a PGP Virtual Disk volume in the Finder
1

Select the mounted PGP Disk (.pgd) file for the volume you want to unmount.

Ctrl+click the .pgd file, or right-click if you are using a two-button mouse. From
the shortcut menu, choose Unmount from the PGP menu. The selected PGP Disk
volume is unmounted.
Tip: If the menu says Mount, then the volume is already unmounted.

Import a PGP Key
PGP keys can be exported from PGP Desktop as .asc files. This is a good way to back up
your keys or exchange your public keys with others. If you have an .asc file on your
system that includes a PGP key that you want on your keyring, you can import it from
the Finder.

The PGP Desktop User Interface
PGP Desktop and the Finder

To import keys from an .asc file in the Finder
1

In the Finder, locate the PGP key (.asc) file with the PGP keys you want to import.

Double-click the selected .asc file. PGP Desktop opens and the Select Keys dialog
box is displayed.

Select the PGP key(s) you want to import, then click OK. The selected key(s) are
added to your keyring.
Tip: You can also import a key by selecting File > Open and browsing to the desired
.asc file.

Add PGP Public Keys to Your Keyring
PGP Desktop stores your PGP keys on keyrings; you always have one private keyring
(.skr) file that holds private keys and one public keyring (.pkr) file that holds public
keys.
If you have a public keyring file (not your active public keyring file) on your system that
holds keys you would like to add to your active keyring, you can add them from the
Finder.
To add PGP public keys from a keyring file in the Finder
1

In the Finder, drag the PGP public keyring (.pkr) or PGP private keyring (.skr)
file and drop it onto your active keyring in the PGP DT window. The Select Keys
dialog box opens and displays the public keys on the selected public keyring file.

Select the keys you want to add to your active keyring, then click OK. You can use
Select All or Select None and the Shift and Command keys to select the desired
keys. The Select Keys dialog disappears and the selected keys are added to your
active keyring.
Tip: In the Finder, double-click the PGP public keyring (.pkr) or PGP private keyring
(.skr) file. The new keyring will appear in PGP Desktop, below your existing
keyrings, as "PGP Public Keyring."

Extract the Contents of a PGP Zip Archive
If you have a PGP Zip archive on your system whose contents you want to extract, you
can do that in the Finder.
To extract the contents of a PGP Zip archive in the Finder
1

In the Finder, select the PGP Zip archive (.pgp) file whose contents you want to
extract.

Ctrl+click the .pgp file, or right-click if you are using a two-button mouse. From
the shortcut menu, choose Decrypt & Verify from the PGP menu. The Enter PGP
Passphrase dialog box is displayed.

The PGP Desktop User Interface
Viewing the PGP Log

Enter the passphrase that protects the PGP Zip archive from which you are
extracting files, then click OK. The file(s) are extracted from the archive to the
same location in the Finder as the archive.

If the archive was signed, the Verification Info dialog is displayed.

Viewing the PGP Log
Use the PGP Log to see what actions PGP Desktop is taking to secure your data. For
more information, see Viewing the PGP Log (on page 103).

Working with PGP Keys

PGP Keys is the feature of PGP Desktop you use to create and maintain your keypair(s)
and the public keys of other PGP Desktop users.
This section describes viewing keys, creating a keypair, distributing your public key,
getting the public keys of others, and working with keyservers.
Note: If you are using PGP Desktop in a PGP Universal Server-managed
environment, your PGP Universal Server administrator may have disabled certain
features. When a feature is disabled, the control item in the left side is not displayed
and the menu and other options for that feature are not available. The graphics
included in this guide depict the default installation with all features enabled. If your
PGP Universal Server administrator has disabled this functionality, this section does
not apply to you.

In This Chapter
Viewing Keys..................................................................................................................38
Creating a Keypair.........................................................................................................40
Protecting Your Private Key ........................................................................................42
Distributing Your Public Key.......................................................................................44
Getting the Public Keys of Others...............................................................................46
Working with Keyservers.............................................................................................48
Using Master Keys.........................................................................................................49

Working with PGP Keys
Viewing Keys

Viewing Keys
To view all of the keys on the local keyring, open PGP Desktop and click the Keys item.

You can also use the Smart Keyrings feature. A Smart Keyring is a set of keys that fits
the criteria you establish. For example, if you frequently send messages to PGP Desktop
users from a particular email domain, you could create a Smart Keying that shows just
the users from that email domain. The default Smart Keyring is My Private Keys.
Some of the more common tasks you may want to perform are available from the PGP
Keys work area. These are:
•

Send an email to the owner of a public key. To do this, Ctrl+click (or right-click) a
public key in any view of the PGP Keys on your keyrings and select Send Email.

•

If you perform a search, and you select a public key found in the search that is not
on your local keyrings, add the key to your keyring. To do this, Ctrl+click (or
right-click) the key and select Add to Default Keyring.

•

To see the properties of any key displayed in the work area, double-click any part
of the key listing to display the Key Info dialog box for that key.

Creating a Smart Keyring
To create a Smart Keyring
1

Open PGP Desktop.

Working with PGP Keys
Viewing Keys

Click the Keys item.

Select File > New > Smart Keyring. The New Smart Keyring dialog box is
displayed.

In the Smart Keyring name field, enter a descriptive name for the Smart Keyring
you are creating.

In the Include keys which match the following conditions menu, select either:

•

Any. Displays keys that match any of the specified criteria (logical “OR”).

•

All. Only displays keys that match all of the specified criteria (logical
“AND”).

In the first matching column, select one of the following:
•

Key is. Displays keys that meet the criteria.

•

Key is not. Displays keys that do not meet the criteria.

•

Name. Displays keys with the specified criteria in the Name.

•

Email. Displays keys with the specified criteria in the Email address.

•

Key ID. Displays keys with the specified criteria in the Key ID.

•

Key Size. Displays keys of the specified Key Size.

•

Creation Date. Displays keys created on the specified Creation Date.

•

Expiration Date. Displays keys that expire on the specified Expiration Date.

The options in the second matching column change based on what you selected in
the first matching column; select between:
•

Public. Matches on public keys only.

•

Private. Matches on private keys only.

•

Revoked. Matches on revoked keys only.

•

Enabled. Matches on enabled keys only.

•

Expired. Matches on expired keys only.

•

Signed by. Matches on keys signed by the specified person.

•

Contains. Matches when key contains specified criteria.

•

Does not contain. Matches when key does not contain specified criteria.

•

Is. Matches when specified criteria (name or date) is met.

•

Is not. Matches when specified criteria is not met.

•

Is at least. Matches when specified criteria is at least the key size entered.

•

Is at most. Matches when specified criteria is no great than the key size
entered.

•

Is on or before. Matches when specified date is on or before the listed date.

•

Is on or after. Matches when specified data is on or after the listed date.

In the text box that is available for some matching items, you can enter text (such
as an email address or a domain; wildcards are allowed), numbers, or dates.

To add extra rows for matching or excluding, click the plus sign icon. Click the
minus sign icon to remove rows.

Working with PGP Keys
Creating a Keypair

Click Save. The Smart Keyring is displayed in the Items list.

When you select this Smart Keyring, only those keys that match these criteria are
listed. The following Smart Keyring, for example, matches the public keys of PGP
Desktop users at your company’s law firm.

Creating a Keypair
You probably already created a PGP keypair for yourself using the PGP Desktop Setup
Assistant or with a previous version of PGP Desktop — but if you have not, you need to
now. Most of the things you do with PGP Desktop require a keypair.
Caution: It is bad practice to keep creating new keys for yourself. A PGP keypair is
like a digital driver’s license or passport; if you create lots of them, you’re going to
end up confusing yourself and those people who want to send you encrypted
messages. It is best to have only one key that contains all the email addresses that
you use. The PGP Global Directory will publish only one key per email address.
If you are using PGP Desktop in a PGP Universal Server-managed environment, keypair
creation may be disabled.
To create a PGP keypair
1

Open PGP Desktop.

From the File menu, select New > PGP Key. The Create a key to secure your
communications dialog box is displayed. Information on this dialog box explains
what a key pair is and how it is used.

To specify advanced properties for your new key, select the Expert Mode check
box. For more information on these settings, see Expert Mode Key Settings (on page
41). Skip this step if you do not want to use Expert Mode.

Click Continue. The Set your key’s contact information dialog box is displayed.

Enter your real name in the Full Name field and your correct email address in the
Email Address field.
Note: It is not absolutely necessary to enter your real name or even your email
address. However, using your real name makes it easier for others to identify you
as the owner of your public key. Also, when you upload your public key to the
PGP Global Directory (which makes it easily available to other PGP Desktop
users), your real email address is required.

Click Continue. The Set your key’s passphrase dialog box is displayed.

Enter a passphrase for the key you are creating, then enter it again to confirm it.
Normally, as an added level of security, the characters you enter for the
passphrase do not appear on the screen. However, if you are sure that no one is
watching, and you would like to see the characters of your passphrase as you type,
click Show Keystrokes.
Caution: Make sure that your passphrase is one that you can easily remember
(without writing it down). Unless your PGP administrator has implemented a
PGP key reconstruction policy for your company, no one, including Symantec
Corporation, can salvage a key with a forgotten passphrase.

Working with PGP Keys
Creating a Keypair

The Passphrase Quality bar provides a basic guideline for the strength of the
passphrase you are creating by comparing the amount of entropy in the
passphrase you type against a true 128-bit random string (the same amount of
entropy in an AES128 key). For more information, see The Passphrase Quality Bar
(on page 180).
8

To save this passphrase in the Mac OS X Keychain, select the check box.

Click Continue. The PGP Key creation summary dialog box is displayed.

If desired, do the following:
•

To show details about the key, select Show Details.

•

To make any changes to your key, click Go Back.

Click Create Key. PGP Desktop generates your new keypair. This process can take
several minutes.

When the key generation process indicates that it is complete, click Finish.

Expert Mode Key Settings
1

When you select Expert Mode on the New PGP Key dialog box, in addition to
specifying your name and email address, you also specify:
•

Key Type. Choose between Diffie-Hellman/DSS and RSA.

Note: Beginning with PGP Desktop 9.0, the older RSA Legacy key format from the
early 1990s is no longer fully supported. You cannot create new PGP keypairs
using the RSA Legacy key format; however, existing RSA Legacy keypairs
continue to be supported in PGP Desktop.
•

Keyserver. Specify a trusted keyserver or .

•

Allowed Compression. Deselect any compression type you do not want the
key you are creating to support.

•

Allowed Ciphers. Deselect any cipher you do not want the key you are
creating to support.

•

Allowed Hashes. Deselect any hash you do not want the keypair you are
creating to support.

•

Preferred Cipher. Select the cipher you want to be used in those cases where
no cipher is specified. Only a cipher that is allowed can be selected as
preferred.

•

Preferred Hash. Select the hash you want to be used in those cases where no
hash is specified. Only a hash that is allowed can be selected as preferred.

•

Key size. Enter from 1024 bits to 4096 bits. The larger the key, the more
secure it is, but the longer it will take to generate.

•

Key Expires. Select Never or specify a date on which the key you are
creating will expire.

Click Continue. The Set Your Key’s Passphrase dialog box is displayed.

Enter the passphrase that you would like to use with this key, then type it again in
the Confirm your passphrase field. It is critical that you keep this passphrase
secret.

Working with PGP Keys
Protecting Your Private Key

Click Continue.

Review the summary information, then click Create Key to begin the key
generation process. PGP Desktop generates your new keypair.
This process can take several minutes.

When the key generation process indicates that it is done, click Next. You are
prompted to add the public key portion of the key you just created to the PGP
Global Directory.

Read the text on the screen and click Next.

Click Skip to prevent the public key from being posted to the PGP Global
Directory. The Completing the PGP Global Directory Assistant screen is displayed.

Click Finish. Your new PGP keypair has been generated. It should be visible in the
PGP Keys Work area. If you don’t see it listed, make sure All Keys or My Private
Keys is selected in the PGP Keys item.

Protecting Your Private Key
Symantec Corporation recommends that you take these actions immediately after you
create your keypair:
Caution: Failure to take these actions could result in a devastating loss of data some
time in the future.
•

Back up a copy of your private key file to another, safe location, in case your
primary copy is ever damaged or lost. See Backing up Your Private Key (on page
43).

•

Reflect on your chosen passphrase to ensure that you chose something that you
will not forget. If you are concerned that you chose a passphrase during the key
creation process that you will not remember, change it RIGHT NOW to something
you will not forget. For information on changing your passphrase, see Changing
Your Passphrase (on page 54, on page 55).

Your private key file is very important because once you have encrypted data to your
public key; only the corresponding private key can be used to decrypt the data. This
holds true for your passphrase as well; losing your private key or the passphrase means
that you will not be able to decrypt data encrypted to the corresponding public key.
When you encrypt information, it is encrypted to both your passphrase and your
private key. You need both to decrypt the encrypted data. Once the data is encrypted,
no one—not even Symantec Corporation—can decrypt the data without your private key
file and your passphrase.
Consider a situation where you have important encrypted data, and then either forget
your passphrase or lose your private key. The encrypted data would be inaccessible,
unusable, and unrecoverable.

Working with PGP Keys
Protecting Your Private Key

Protecting Keys and Keyrings
Besides making backup copies of your keys, you should be especially careful about
where you store your private key. Even though your private key is protected by a
passphrase that only you should know, it is possible that someone could discover your
passphrase and then use your private key to decipher your email or forge your digital
signature. For instance, somebody could look over your shoulder and watch the
keystrokes you enter or intercept them on the network or over the Internet.
To prevent anyone who might happen to intercept your passphrase from using your
private key, store your private key only on your own computer. If your computer is
attached to a network, make sure that your files are not automatically included in a
system-wide backup where others might gain access to your private key. Given the ease
with which computers are accessible over networks, if you are working with extremely
sensitive information, you may want to keep your private key on a diskette, which you
can insert like an old-fashioned key whenever you want to read or sign private
information.
As another security precaution, consider assigning a different name to your private
keyring file and then storing it somewhere other than in the default location. Use the
Keys tab of the Options dialog box to specify a name and location for your private and
public keyring files.
Your private and public keys are stored in separate keyring files. You can copy them to
another location on your hard drive or to a diskette. By default, the private keyring
(secring.skr) and the public keyring (pubring.pkr) are stored along with the other
program files in your “PGP” folder; you can save your backups in any location you like.
Keys generated on a smart card cannot be backed up because the private portion of your
keypair is non-exportable. (Keys can be generated on a smart card on Windows systems
only.)
You can configure PGP Desktop to back up your keyrings automatically after you close
PGP Desktop. Your keyring backup options can be set in the Keys tab of the Options
dialog box (for Windows) and in the Keys section of the Preferences dialog box (for Mac
OS X).

Backing up Your Private Key
To back up your private key
1

In the Smart Keyrings item, click My Private Keys.

Select the icon representing your keypair.

From the File menu, select Export.

Type a name for the file in the Save As field and specify a location in the Where
field.

Select the Include Private Key(s) check box. This is important, because if you do
not do this, only your public key will be exported.

Click Save.

Working with PGP Keys
Distributing Your Public Key

Copy the file to a secure location. This may be a CD which you carefully archive,
another personal computer, or a USB flash drive that you keep in a safe location.
Please remember not to distribute this file to others, as it contains both your
private key and your public key.
Note: If you are in a PGP Universal Server-managed environment and your key mode
is SKM, you cannot export your key using this method. To export your keypair, ask
your PGP Universal Server administrator to export it from the management console.
To determine what your key mode is, see Key Modes (on page 101).

What if You Lose Your Key?
If you lose your key and do not have a backup copy from which to restore your key, you
will never again be able to decrypt any information encrypted to your key. You can,
however, reconstruct your key if your PGP administrator has implemented a key
restoration policy for your company. For more information, see PGP Key Reconstruction
(see "Reconstructing Keys with PGP Universal Server" on page 70, "If You Lost Your Key
or Passphrase" on page 69) and contact your PGP administrator.

Distributing Your Public Key
After you create your PGP Desktop keypair, you need to get your public key to those
with whom you intend to exchange encrypted messages.
You make your public key available to others so they can send you encrypted
information and verify your digital signature; and you need their public key to send
encrypted messages to them.
You can distribute your public key in various ways:
•

Publish your key on the PGP Global Directory (see "Placing Your Public Key on a
Keyserver" on page 44).
Generally none of the other methods are necessary once your key is published to
this directory.

•

Include your public key in an email message (see "Including Your Public Key in an
Email Message" on page 45).

•

Export your public key or copy it to a text file (see "Exporting Your Public Key to a
File" on page 46).

On Windows systems, you can also:
•

Copy from a Smart Card directly to someone's keyring.

Placing Your Public Key on a Keyserver
The best method for making your public key available is to place it on a public
keyserver, which is a large database of keys, where anyone can access it. That way,
people can send you encrypted email without having to explicitly request a copy of your
key. It also relieves you and others from having to maintain a large number of public
keys that you rarely use.

Working with PGP Keys
Distributing Your Public Key

There are a number of keyservers worldwide, including the PGP Global Directory,
where you can make your key available for anyone to access. If you are using PGP
Desktop in a domain protected by a PGP Universal Server, your PGP administrator will
have preconfigured PGP Desktop with appropriate settings.
When you’re working with a public keyserver, keep these things in mind before you
send your key:
•

Is this the key you intend to use? Others attempting to communicate with you
might encrypt important information to that key. For this reason, we strongly
recommend you only put keys on a keyserver that you intend for others to use.

•

Will you remember your passphrase for this key so you can retrieve data
encrypted to it or, if you don’t want to use the key, so you can revoke it?

•

Other than the PGP Global Directory, once a key is up there, it’s up there. Some
public keyservers have a policy against deleting keys. Others have replication
features that replicate keys between keyservers, so even if you are able to delete
your key on one server, it could reappear later.

Most people post their public key to the PGP Global Directory right after they create
their keypair. If you have already posted your key to the PGP Global Directory, you do
not need to do it again. Under most circumstances, there is no need to publish your key
to any other keyserver. Note also that other keyservers may not verify keys, and thus
keys found on other keyservers may require significantly more work on your part to
contact the key owner for fingerprint verification.
To manually send your public key to a keyserver
1

Open PGP Desktop.

Ctrl+click the keypair whose public key you want to send to the keyserver.

Select Send Key To Server, then select the keyserver you want to send the public
key to from the list. If the keyserver you want to send your public key to is not on
the list, see Working with Keyservers (on page 48).

Once you place a copy of your public key on a keyserver, it’s available to people who
want to send you encrypted data or to verify your digital signature. Even if you don’t
explicitly point people to your public key, they can get a copy by searching the
keyserver for your name or email address.
Many people include the Web address for their public key at the end of their email
messages. In most cases, the recipient can just double-click the address to access a copy
of your key on the server. Some people even put their PGP fingerprint on their business
cards for easier verification.

Including Your Public Key in an Email Message
Another convenient method of delivering your public key to someone is to include it
with an email message.
When you send someone your public key, be sure to sign the email. That way, the
recipient can verify your signature and be sure no one has tampered with the
information along the way. Of course, if your key has not yet been signed by any trusted
introducers, recipients of your signature can only truly be sure the signature is from
you by verifying the fingerprint on your key.

Working with PGP Keys
Getting the Public Keys of Others

To include your public key in an email message
1

Open PGP Desktop.

Open your email client, create a new message, and address it to the person to
whom you are sending your public key.

From PGP Desktop, drag and drop your keypair onto the body of the email
message.

Send the message.

If this method does not work for you, you can open PGP Desktop, select your keypair,
then select Edit > Copy. Open an email message, then paste the public key into the body
of the message. With some email applications you can simply drag your key from PGP
Desktop into the text of your email message to transfer the public key information.

Exporting Your Public Key to a File
Another method of distributing your public key is to export it to a file and then make
this file available to the person with whom you want to communicate securely.
There are three ways to export or save your public key to a file:
•

Select your keypair, then select File > Export. Enter a name and a location for the
file, then click Save. Be sure not to include your private key along with your public
key if you plan on giving this file to others.

•

Ctrl+click the key you want to save to a file, select Export from the list, enter a
name and a location for the file, then click Save. Be sure not to include your
private key along with your public key if you plan on giving this file to others.

•

Select your keypair, then select Edit > Copy. Open a text editor and select Paste to
insert the key information into the text file, and save the file. You can then email
or give the file to anyone you like. The recipient needs to use PGP Desktop on his
or her system to retrieve the public key portion.

Getting the Public Keys of Others
Just as you need to distribute your public key to those who want to send you encrypted
mail or verify your digital signature, you need to obtain the public keys of others to
send them encrypted mail or verify their digital signatures.
There are multiple ways to obtain someone’s public key:
•

Automatically retrieve the verified key from the PGP Global Directory

•

Find the key manually on a public keyserver

•

Automatically add the public key to your keyring directly from an email message

•

Import the public key from an exported file

•

Get the key from your organization’s PGP Universal Server

Working with PGP Keys
Getting the Public Keys of Others

Public keys are just blocks of text, so they are easy to add to your keyring by importing
them from a file or by copying them from an email message and then pasting them into
your public keyring in PGP Desktop.

Getting Public Keys from a Keyserver
If the person to whom you want to send encrypted mail is an experienced PGP Desktop
user, it is likely that a copy of his or her public key is on the PGP Global Directory or
another public keyserver. This makes it very convenient for you to get a copy of the
most up-to-date key whenever you want to send him or her mail and also relieves you
from having to store a lot of keys on your public keyring.
There are a number of public keyservers, such as the PGP Global Directory maintained
by Symantec Corporation, where you can locate the keys of most PGP users. If the
recipient has not pointed you to the Web address where his or her public key is stored,
you can access any keyserver and do a search for the user’s name or email address. This
may or may not work, as not all public keyservers are regularly updated to include the
keys stored on all the other servers.
If you are in a domain protected by a PGP Universal Server, then your PGP
administrator may direct you to use the keyserver built into the PGP Universal Server.
In this case, your PGP Desktop software is probably already configured to access the
appropriate PGP Universal Server.
Similarly, the PGP Universal Server is configured by default to communicate with the
PGP Global Directory. Thus, the PGP ecosystem distributes the load of key lookup and
verification.
To get someone’s public key from a keyserver
1

Open PGP Desktop.

Click the PGP Global Directory item or the item of another keyserver you want to
search. The Search for Keys screen is displayed in the Work area.

Specify your search criteria, then click Search.
•

If the keyserver you want to search is not shown, from the Keys menu, select
Add Keyserver, and configure it.

•

You can search for keys on a keyserver by specifying values for multiple key
characteristics. You can also search for exclusions, such a using “User ID is
not Charles” as your criteria.

The results of the search appear.
4

If the search found a public key you want to add to your keyring, Ctrl+click it and
select Add To Default Keying. The selected key is added to your keyring.
Tip: If you set the search criteria to look for a very common name (for example,
'Name', 'contains', "John"), only the first match found is returned. This is by design,
to prevent phishing (or harvesting keys from a keyserver). For common names or
domains, you may have to enter the entire name or email address in order to find the
correct key.

Working with PGP Keys
Working with Keyservers

Getting Public Keys from Email Messages
A convenient way to get a copy of someone’s public key is to have that person attach it
to an email message.
To add a public key attached to an email message
1

Open the email message.

Double-click the .asc file that includes the public key. PGP Desktop recognizes
the file format and opens the Select key(s) dialog box.

If asked, specify to open the file.

Select the public key(s) you want to add to your keyring and click Import.

Working with Keyservers
PGP Desktop understands the following kinds of keyservers:
•

PGP Universal keyservers. If you are using PGP Desktop in a domain protected by
a PGP Universal Server, PGP Desktop is pre-configured to only communicate with
the keyserver built into the PGP Universal Server with which it has a relationship.
To PGP Desktop, this is a trusted keyserver, and PGP Desktop will automatically
trust any key it finds on this keyserver unless the PGP Universal Server tells PGP
Desktop that the key is not trusted—this can happen, for instance, when verifying
signatures from remote keys.

•

The PGP Global Directory. If you are using PGP Desktop outside of a domain
protected by a PGP Universal Server, PGP Desktop is pre-configured to
communicate with the PGP Global Directory.
The PGP Global Directory is a free, public keyserver hosted by Symantec
Corporation. It provides quick and easy access to the universe of PGP keys. It uses
next-generation keyserver technology that verifies the key associated with each
email address (so that the keyserver doesn’t get clogged with unused keys,
multiple keys per email address, forged keys, and other problems that plagued
older keyservers) and it lets you manage your own keys, including replacing your
key, deleting your key, and adding email addresses to your key. Using the PGP
Global Directory significantly enhances your chances of finding the public key of
someone with whom you want to send secured messages.
To PGP Desktop, the PGP Global Directory is a trusted keyserver, and PGP Desktop
will automatically trust any key it finds there. During the initial connection to the
PGP Global Directory, the PGP Global Directory Verification Key is downloaded,
signed, and trusted by the key you publish to the directory. All of the keys verified
by the PGP Global Directory are thus considered valid by your PGP Desktop.

•

PGP Universal Services Protocol. The PGP Universal Services Protocol (USP) is a
SOAP protocol operating over standard HTTP/HTTPS ports. This is the default key
lookup mechanism. If you are in a PGP Universal Server-managed environment,
all key search requests as well as all other communications between the the PGP
Universal Server and PGP Desktop use PGP USP.

Working with PGP Keys
Using Master Keys

•

Other keyservers. In most cases, other keyservers are other public keyservers.
However, you may have access, through your company or some other means, to a
private keyserver.

For more information about working with keyservers, see Keys Preferences (on page
167).

Using Master Keys
The Master Key List is a set of keys that you want added by default any time you are
selecting keys for messaging, disk encryption, and PGP Zip. This saves you the step of
dragging the keys that you regularly use into the Recipients field.

To use the Master Key List, select the Use Master Key List checkbox. You cannot add or
remove keys from the Master Key List unless this box is selected.
Note: If you generated your key using the Setup Assistant, your key is automatically
added to the Master Key list. If you skipped key generation and imported your key
into PGP Desktop, your key is not automatically added to the list.
T

Adding Keys to the Master Key List
To add keys to the Master Key List
1

Open PGP Desktop.

Select PGP > Preferences.

Select the Master Keys icon.

Click the plus sign icon beneath the key list. The Select Master Keys dialog box is
displayed.

From the Name list on the left, select the key(s) that you want to use. Use
Shift+click or Cmd+click to select multiple keys.

Working with PGP Keys
Using Master Keys

After selecting the keys you want, click OK. The keys you have selected appear in
the Master Key List.

Deleting Keys from the Master Key List
To remove keys from the Master Key List
1

Open PGP Desktop.

Select PGP > Preferences.

Select the Master Keys icon.

Select the key(s) that you want to remove. You can Shift+click or Cmd+click to
select multiple keys.

Click the minus sign icon beneath the key list. The key(s) are removed.

Managing PGP Keys

This section describes how to manage keys with the PGP Desktop application.
Note: If you are using PGP Desktop in a PGP Universal Server-managed
environment, your PGP Universal Server administrator may have disabled certain
features. When a feature is disabled, the control item in the left side is not displayed
and the menu and other options for that feature are not available. The graphics
included in this guide depict the default installation with all features enabled. If your
PGP Universal Server administrator has disabled this functionality, this section does
not apply to you.

In This Chapter
Examining and Setting Key Properties ......................................................................51
Adding and Removing Photographs...........................................................................52
Managing User Names and Email Addresses on a Key............................................53
Importing Keys and X.509 Certificates ......................................................................54
Changing Your Passphrase ..........................................................................................54
Deleting Keys, User IDs, and Signatures ...................................................................55
Disabling and Enabling Public Keys ...........................................................................56
Verifying a Public Key ..................................................................................................56
Signing a Public Key......................................................................................................57
Granting Trust for Key Validations............................................................................59
Working with Subkeys..................................................................................................60
Working with ADKs ......................................................................................................64
Working with Revokers ................................................................................................66
Splitting and Rejoining Keys .......................................................................................67
If You Lost Your Key or Passphrase ...........................................................................69
Protecting Your Keys ....................................................................................................73

Examining and Setting Key Properties
The Key Info dialog box displays everything there is to know about a key. The PGP Keys
Work Area can display these important details about your keys:
•

Name

•

Email address

•

Validity

•

Size

•

KeyID

Managing PGP Keys
Adding and Removing Photographs

•

Trust

•

Creation date

•

Expiration date

•

ADK

•

Status

•

Key description

•

Key usage
Note: If you are in a PGP Universal Server-managed environment and your key mode
is SKM, you cannot make changes to your key. In addition, SKM keys are set to
never expire. To determine what your key mode is, see Key Modes (on page 101).

To view a key’s properties
1

Open PGP Desktop, then click the Keys item. All keys on your keyring appear.

Double-click the key with the properties you want to view. The Key Properties
dialog box for the key you selected is displayed.

Adding and Removing Photographs
You can include a photograph to your Diffie-Hellman/DSS and RSA keys.
Note: When you add or change key information, be sure to update it on the keyserver
so that your most current key is always available.
Caution: Although you can view for verification the photograph accompanied with
someone’s key, the digital fingerprint is the final word. Always check and compare it.
To add your photograph to your key
1

Open PGP Desktop, then click My Private Keys.

Double-click the private key to which you are adding the photo. The Key Info
dialog box for the selected key is displayed.

Click the plus sign icon under the current photo for the key. The Add Photo dialog
box is displayed.

Drag and drop, or paste, your photograph into the blank area of the Add Photo
dialog box.
Note: The photograph can be from the Clipboard, a JPG, or BMP file. For
maximum picture quality, crop the picture to 120 x 144 pixels before adding it. If
you do not do this, PGP Desktop scales it for you.

Click OK. The Enter PGP Passphrase dialog box is displayed, unless the passphrase
for the key you are modifying is cached.

Enter your passphrase for the key you are modifying, then click OK. Your photo ID
is added to your private key.

Managing PGP Keys
Managing User Names and Email Addresses on a Key

To view an enlargement of the photo
•

Click the magnifying glass icon under the existing photo. A window displaying an
enlarged version of the photo ID appears. To remove the enlargement, click inside
the window.

To delete a photo ID
1

Click the minus sign icon under the existing photo. A confirmation dialog box is
displayed.

Confirm that this is your choice. The photo is removed from the key.

To copy a photo ID
•

Right-click the existing photo on the Key Properties dialog box and select Copy
Photo ID. You can then paste the photo into another key or into a graphics
program.

Managing User Names and Email Addresses on a Key
PGP Desktop supports multiple user names and email addresses on your keypair. These
names and email addresses help others find your key so that they can send you
encrypted messages.
To add a new user name/address to your keypair
1

Open PGP Desktop, then double-click the appropriate key. The Key Info dialog box
for the key you double-clicked is displayed.

Click Add Email Address. The Add Name dialog box is displayed.

Enter the new Full Name and Email Address in the appropriate fields, then click
OK. The Enter PGP Passphrase dialog box is displayed, unless the passphrase for
the key you are modifying is cached.

Enter the private key passphrase of the key you are modifying, then click OK. The
new name is added to the end of the user name list associated with the key.
Note: When you add or change information in your keypair, always synchronize it
with your keyserver so that your most current key is always available.

To delete a name/email address from your keypair
1

From the list of keys, click the plus sign to the left of the key name to expand the
key.

Select the user ID you want to delete.

Press the Delete key on your keyboard. A confirmation dialog box is displayed.

Managing PGP Keys
Importing Keys and X.509 Certificates

Tip: You can also select Edit > Delete (on Windows systems) or Edit > Clear (on
Mac OS X systems).
4

Click Delete. The user ID is deleted.

Importing Keys and X.509 Certificates
You can import PGP public keys and PKCS-12 X.509 certificates (a digital certificate
format used by most Web browsers) to your PGP Desktop keyring, as well as PKCS-7
public X.509 certificates. You can also import Privacy Enhanced Mail (PEM) format
X.509 certificates from your browser by copying and pasting into your public keyring.
There are many ways to import someone’s PGP public key and add it to your keyring.
These methods include:
•

Double-clicking the file on your system. If PGP Desktop recognizes the file format,
it will open and ask if you want to import the key(s) in the file.

•

Choosing to import the key file in PGP Desktop.

•

Dragging the file containing the public key onto the PGP Keys window.

Importing X.509 Certificates Included in S/MIME Email Messages
If an X.509 certificate is included in an S/MIME email message sent to you, you can
have PGP Desktop import the certificates to your key ring. The same settings you have
specified when public keys are found apply to these certificates. If specified, PGP
Desktop extracts and then imports the X.509 certificate to your keyring. If you want to
encrypt email using imported certificates, be sure to manually sign the certificate.
To import X.509 certificates, select PGP > Preferences. and select the Keys option.
Then select Ask to save to my keyring or Save keys to my keyring.

Changing Your Passphrase
It’s a good practice to change your passphrase at regular intervals, perhaps every three
months. More importantly, you should change your passphrase the moment you think
it has been compromised, for example, by someone looking over your shoulder at the
keyboard as you typed it in.
To change the passphrase for a split key, you must rejoin it first.
Tip: Changing your passphrase on your key does not change the passphrase on any
copies of the key (such as backups you may have made). If you think your key has
been compromised, Symantec Corporation recommends that you shred any previous
backup copies and then make new backups of your key.

Managing PGP Keys
Deleting Keys, User IDs, and Signatures

If you are in a PGP Universal Server-managed environment and your key mode is SKM,
you cannot change the passphrase for your key. SKM keys are protected by a randomly
generated passphrase (that is itself protected) and you are never prompted to enter a
passphrase for an SKM key. To determine what your key mode is, see Key Modes (on
page 101).
To change your private key passphrase
1

Open PGP Desktop, then double-click the appropriate key. The Key Info dialog box
for the key you double clicked is displayed.

Click Change Passphrase, then select Change Passphrase from the list of
commands displayed. The Enter PGP Passphrase dialog is displayed.

Enter the current passphrase for the private key, then click OK. The Confirm PGP
Passphrase dialog box is displayed.

Enter your new passphrase in the first text field.

Re-enter your passphrase in the Confirmation field.
The Passphrase Quality bar provides a basic guideline for the strength of the
passphrase you are creating by comparing the amount of entropy in the
passphrase you type against a true 128-bit random string (the same amount of
entropy in an AES128 key). For more information, see The Passphrase Quality Bar
(on page 180).

Click OK. An information dialog box is displayed, informing you the passphrase
has been changed.

Click OK. The passphrase is changed.
Caution: If you are changing your passphrase because you feel that it has been
compromised, it is recommended that you shred all backup keyrings, then make a
backup copy of the key with the new passphrase.

Deleting Keys, User IDs, and Signatures
PGP Desktop gives you control over the keys on your keyrings, as well as the user IDs
and signatures on those keys.
With public keys on your keyrings, you can delete entire keys, any user IDs on a key,
and any or all signatures on a key.
With your keypairs, you can delete entire keypairs or any or all signatures, as well as
delete user IDs from a keypair as long as that is not the only user ID on the keypair.
Note, however, that you cannot delete a user ID on a key if it is the only user ID, and you
cannot delete self-signatures from keys.
To delete a key from your PGP keyring
1

Open PGP Desktop, then click the Keys item. All keys on your keyring appear.

Do one of the following:
•

To delete a key, select the key, select Edit > Clear, then click OK on the
Confirmation dialog box. The key is deleted from your keyring.

Managing PGP Keys
Disabling and Enabling Public Keys

•

To delete a user ID (from a public key) or signature, click the triangle to the
left of the key with the User ID or Signature that you want to delete to
display the user IDs and signatures. When you see the user ID or signature
you want to delete, click the User ID, select Edit > Clear, then click OK on the
Confirmation dialog box. The user ID or signature is deleted.
Remember that you cannot delete a user ID from a keypair.

Disabling and Enabling Public Keys
Sometimes you may want to temporarily disable a public key on your keyring, which
can be useful when you want to retain a public key for future use, but you don’t want it
cluttering up your recipient list every time you send mail.
You cannot disable your keypairs.
To disable a public key
1

Open PGP Desktop, then click the Keys item. All keys on your keyring appear.

Double-click the public key you want to disable. The Key Info dialog box for the
key you selected is displayed.

Locate the Enabled field in the Key Properties.
•

If the current Enabled setting is Yes, the key is enabled. To disable the key,
click Yes once. The Enabled field changes to No; the key is disabled.

•

If the current Enabled setting is No, the key is disabled. To enable the key,
click No once. The Enabled field changes to Yes and the key is enabled.

A disabled key cannot be used to encrypt, sign, decrypt, or verify.
Tip: You can also synchronize keys on your keyring with the PGP Universal Server.
This option is used primarily to enable/disable public keys on your keyring. To do
this, right-click (or Ctrl+click) a key and choose Synchronize.

Verifying a Public Key
It is difficult to know for certain whether a public key belongs to a particular individual
unless that person physically hands the key to you on a removable media or you get the
key from the PGP Global Directory. Exchanging keys on removable media is not usually
practical, especially for users who are located many miles apart.
So the question remains: how can I make sure the public key I got from a public
keyserver (not the PGP Global Directory) is really the public key of the person listed on
the key? The answer is: you have to check the key’s fingerprint.
There are several ways to check a key’s fingerprint, but the safest is to call the person
and have them read the fingerprint to you over the phone. Unless the person is the
target of an attack, it is highly unlikely that someone would be able to intercept this
random call and imitate the person you expect to hear on the other end. You can also
compare the fingerprint on your copy of someone’s public key to the fingerprint on
their original key on a public server.

Managing PGP Keys
Signing a Public Key

The fingerprint can be viewed in two ways: in a unique list of words or in its
hexadecimal format.
To check the digital fingerprint of a public key
1

Open PGP Desktop, then click the Keys item. All keys on your keyring appear.

Double-click the public key with the fingerprint that you want to check. The Key
Info dialog box is displayed.

Locate the Digital Fingerprint in the second section of the Key Info dialog box.
If necessary, click the triangle to face downward and display the fingerprint,
which is shown either in hexadecimal format (10 sets of four characters per set) or
word list format (four columns with five unique words per column).

Compare the fingerprint on the key with the original fingerprint. If the two are the
same, then you have the real key—otherwise, you likely do not.
The word list is made up of special authentication words that PGP Desktop uses
and are carefully selected to be phonetically distinct and easy to understand
without phonetic ambiguity. The word list serves a similar purpose as the military
alphabet, which allows pilots to convey information distinctly over a noisy radio
channel.

If you have a forged key, delete it.

Open your Web browser, navigate to the PGP Global Directory
(https://keyserver.pgp.com), and search for the real public key.

Signing a Public Key
When you create a keypair, the keys are automatically signed. Similarly, once you are
sure a key belongs to the correct person, you can sign that person’s public key,
indicating that you have verified the key. When you sign someone’s public key, a
signature icon along with your user name is shown attached to that key.
If you import a keypair from a backup or from a different computer, that keypair needs
to be signed.
Note: If you are using PGP Desktop in a PGP Universal Server-managed
environment, key signing may be disabled.
To sign a key
1

Open PGP Desktop, then click the Keys item. All keys on your keyring appear.

Select the key you want to sign, then from the Keys menu, select Sign. The Sign
Key dialog box is displayed with the user name/email address and hexadecimal
fingerprint displayed in the text box.
Tip: You can also Ctrl+click the key (or right-click it if you have a two-button
mouse). When the shortcut menu is displayed, select Sign.

Under Sign With Key, click to display and select which of your keys you want to
sign with.

Managing PGP Keys
Signing a Public Key

To allow your signature to be exported with this key, select Allow signature to be
exported.
An exportable signature is one that is allowed to be sent to servers and travels
with the key whenever it is exported. The checkbox indicates your approval that
your signature be exported.

In the Select Items to Sign box, verify that you are signing the right key.

If you want to configure additional options, such as such as signature type and
signature expiration, click Options.

Choose a Signature Type to sign the public key with. Your choices are:
•

Non-exportable. Use this signature when you believe the key is valid, but
you don’t want others to rely on your certification. This signature type
cannot be sent with the associated key to a keyserver or exported in any way.

•

Exportable. Use exportable signatures in situations where your signature is
sent with the key to the keyserver, so that others can rely on your signature
and trust your keys as a result. This is equivalent to checking the Allow
signature to be exported checkbox on the Sign Keys menu.

•

Meta-Introducer Non-Exportable. Certifies that this key, and any keys
signed by this key with a Trusted Introducer Validity Assertion, are fully
trusted introducers to you. This signature type is non-exportable.

•

Trusted Introducer Exportable. Use this signature in situations where you
certify that this key is valid, and that the owner of the key should be
completely trusted to vouch for other keys. This signature type is exportable.
You can restrict the validation capabilities of the trusted introducer to a
particular email domain.

In the Expires field, select Never if you do not want this signature to expire.
Otherwise, select a date for it to expire.

In the Advanced field, specify a maximum depth for trust and a domain
restriction:
•

The Maximum Depth option enables you to identify how many levels deep
you can nest trusted-introducers. For example, if you set this to 1, there can
only be one layer of introducers below the meta-introducer key.

•

If you want to limit the trusted introducer’s key validation capabilities to a
single domain, enter the domain name in the Domain Restriction text box.

Click Sign. The Enter PGP Passphrase dialog box is displayed (if your passphrase
was not saved in the Keychain).

Type the passphrase of the signing key, if required. PGP Desktop does not ask you
to type your passphrase if it is cached.

Click OK. The key is signed.

Revoking Your Signature from a Public Key
You may, on occasion, want or need to revoke your signature from a key on your
keyring.

Managing PGP Keys
Granting Trust for Key Validations

To revoke your signature
1

Open PGP Desktop, then click the Keys item. All keys on your keyring appear.

Click the triangle to the left of the key from which you want to revoke your
signature. The signatures appear.

Click your signing key.

Select Edit > Revoke. A confirmation dialog box is displayed.

Verify that the Key ID and Name are the correct key (from which you want to
revoke your signature) and click OK. The PGP Enter PGP Passphrase for Key
dialog box is displayed.

Enter your passphrase and click OK. Your signature is revoked from the key.

Granting Trust for Key Validations
Besides certifying that a key belongs to someone, you can assign a level of trust to the
owner of the keys indicating how well you trust them to act as an introducer for others,
whose keys you may get in the future.
This means that if you ever get a key from someone that has been signed by an
individual whom you have designated as trustworthy, the key is considered valid even
though you have not done the check yourself.
You must sign a key before you can set a trust level for it.
Public keys can be None, Marginal, or Trusted. Your keypairs can be None or Implicit
(meaning it is your own key and thus you trust it completely). You shouldn’t have
anyone else’s keypairs.
For more information about trusting keys, see An Introduction to Cryptography.
Note: If you are using PGP Desktop in a PGP Universal Server-managed
environment, the ability to grant trust to keys may be disabled.

To grant trust to a key
To grant trust to a key
1

Open PGP Desktop, then click the Keys item. All keys on your keyring appear.

Double-click the key for which you are granting trust. The Key Info dialog box is
displayed.

In the General Information section, click the current Trust field setting. A menu
of trust settings is displayed.

Select the desired setting.
Note: Selecting a Trust setting of None or Marginal is not intended to indicate that
an owner of a key is untrustworthy or dishonest. It means that you do not have
enough information to be sure that a key’s owner or source is genuine.

Managing PGP Keys
Working with Subkeys

Working with Subkeys
A PGP Desktop keypair consists of these elements:
•

the Master Key, for signing only;

•

one mandatory Subkey for encryption;

•

one or more optional Separate Subkey(s) for signing, encryption, or
signing/encryption.

The Master Key is used by default for signing, while a subkey is always used for
encryption. This can improve the security of a PGP Desktop keypair, as a separate
encryption subkey can be revoked, removed, or added to the PGP Desktop keypair
without affecting the Master Key or the signatures on it.
In addition to the Master Key and the mandatory encryption subkey, you have the
option of creating one or more additional subkeys for your PGP Desktop keypair. You
can create any combination of subkeys that can be used for encryption only, for signing
only, or for both encryption and signing.

Managing PGP Keys
Working with Subkeys

You can view the subkeys of a keypair from the Key Properties dialog box. The Usage
column indicates the function that a subkey performs:

Key

Description
Encryption subkeys display a blue padlock symbol.
Signing subkeys display a blue pen symbol.
Subkeys used for both encryption and signing display both
symbols.
The default encryption subkey displays a small green
checkmark in the upper left corner.
The default signing subkey displays a small green check mark in
the upper left corner.

Managing PGP Keys
Working with Subkeys

Using Separate Subkeys
Here are some examples of how additional separate subkeys can be useful:
•

Multiple encryption subkeys that are valid during different portions of the
keypair’s lifetime can increase security. You can create encryption subkeys that
have the Start and Expiration dates set so that only one encryption subkey at a
time is valid. For example, you could create several encryption subkeys that are
valid only during one future year (make sure you specify correct dates). The
Encryption Subkey in use then changes with the new year. This can be a useful
security measure, as it provides an automatic way to switch to a new encryption
key periodically without having to recreate and distribute a new public key.
Expired subkeys display a key icon with a red clock.

•

Separate signing subkeys are needed in regions where separate subkeys for
signing are required for legally-binding digital signatures.

The separate subkeys that you can create depend on the type of keypair that you are
working with:
•

For RSA keypairs, you can create subkeys for encryption, signing, and
encryption/signing.

•

For Diffie-Hellman/DSS keypairs, you can create subkeys for encryption or
signing, but you cannot create subkeys that both encrypt and sign.

•

For older PGP Legacy keypairs, subkeys are not supported.

Viewing Subkeys
You can view and change the subkey information on your keypairs. However, you can
only view subkey information on the public keys on your keyring.
To see what subkeys are on a key
1

Open PGP Desktop, then click the Keys item. All keys on your keyring appear.

Double-click the key with the properties you want to view. The Key Properties
dialog box for the key you selected is displayed.

Click the triangle to the left of Subkeys. The Subkeys information for this key is
displayed.

Creating New Subkeys
Most likely you will create new subkeys in the manner described in this section.
However, you can also create subkeys when you first install PGP Desktop and are using
the New Key wizard. For more information, see Using PGP Desktop for the First Time (on
page 12).

Managing PGP Keys
Working with Subkeys

To create new subkeys for a keypair
1

In the Subkeys section of the Key Properties dialog box, click the plus sign icon.
The New Subkey dialog box is displayed.

In the Use this subkey for area, select Encryption, Signing, or Encryption and
Signing, depending on how you want to use the new subkey.

In the Key Size field, type a key size from 1024 to 4096 bits.

In the Start Date field, enter a date on which the subkey you are creating becomes
effective.

In the Expiration Date field, select Never, or specify a date. This information
controls when the subkey expires.
Note: To avoid confusion when maintaining more than one subkey on your
keypair, try not to overlap the start and expiration dates of your subkeys.

Click Create. The Passphrase dialog box is displayed.

Enter your passphrase and then click OK. The subkey is created.
Note: When you add or change information in your keypair, update it on the
keyserver so that your most current key is always available. With the key selected in
the Keys list, from the Keys menu, select Update Selection.

Specifying Key Usage for Subkeys
Each subkey can have its own key usage properties. For example, one subkey could be
used for PGP WDE only, and another could be used for all other PGP Desktop functions.
An example of why you would want to set the key usage of a key is when you want to
use a key for disk encryption only but you do not want to receive encrypted email. If
you distribute your public key that does not allow for PGP Messaging, then email sent
by another user would not be encrypted to your public key.
Note: If you are in a PGP Universal Server-managed environment and your key mode
is SKM, you cannot make changes to the key usage flags. To determine what your key
mode is, see Key Modes (on page 101).
To specify key usage
1

Open PGP Desktop, then click the Keys item. All keys on your keyring appear.
Double-click the key with the properties you want to view. The Key Properties
dialog box for the key you selected is displayed.

Click the Subkeys heading in the Key Properties dialog box. The Subkeys for this
key are displayed.

Double-click the subkey you want to change.

Click the arrow next to Subkey Usage Edit. The usage properties for the key are
displayed.

In the list displayed, select the PGP Desktop functions for which this key can be
used. A check next to the item indicates the key can be used for that function.

Managing PGP Keys
Working with ADKs

Click Close to save the subkey properties.

Click Close again to save the key properties.

Revoking Subkeys
To revoke a subkey
1

In the Subkeys section of the Key Properties dialog box, select the subkey you
want to revoke.

Click Revoke (backslash-circle icon above the subkey list). A confirmation dialog
box is displayed.

Click OK to revoke the subkey. The Passphrase dialog box is displayed.

Type your passphrase, then click OK. The subkey is revoked and the icon changes
to a key with a red circle/slash.

Removing Subkeys
To remove a subkey
1

In the Subkeys section of the Key Properties dialog box, select the subkey you
want to remove.

Click Remove (a minus sign icon above the subkey list). A confirmation dialog box
is displayed.

Click OK to remove the subkey. The subkey is removed.

Working with ADKs
An additional decryption key (ADK) is a key generally used by security officers of an
organization to decrypt messages that have been sent to or from employees within the
organization.
Messages encrypted by a key with an ADK are encrypted to the public key of the
recipient and to the ADK, which means the holder of the ADK can also decrypt the
message.
ADKs are rarely used or needed outside of a PGP Universal Server-managed
environment. Although your PGP administrator should not ordinarily need to use the
additional decryption keys, there may be circumstances when it is necessary to recover
someone’s email. For example, if someone is injured and out of work for some time, or if
email records are subpoenaed by a law enforcement agency and the corporation must
decrypt mail as evidence for a court case.
You can only modify ADKs on your keypairs.

Managing PGP Keys
Working with ADKs

Adding an ADK to a Keypair
To add an ADK to a keypair
1

Open PGP Desktop, then click the Keys item. All keys on your keyring appear.

Double-click the keypair to which you are adding the ADK. The Key Info dialog box
for the key you double-clicked is displayed.

If necessary, click the triangle icon, on the left side of the Additional Decryption
Keys section, so that it is pointing downward. The ADK information for this key is
displayed, if it has been configured.

Click the plus sign icon on the right side of the Additional Decryption Keys
section.

From the list displayed, select the key you want to use as the ADK.

Click OK. The PGP Enter PGP Passphrase for Key dialog box is displayed.

Enter the passphrase for the key to which you are adding the ADK, then click OK.
The ADK is added.

Updating an ADK
To update an ADK
1

Select the ADK you want to update from the list of ADKs. The selected ADK
highlights.

Click the down arrow icon. The ADK is updated.

Removing an ADK
To remove an ADK
1

Select the ADK you want to remove from the list of ADKs. The selected ADK
highlights.

Click the minus sign icon. A PGP Warning dialog box is displayed, asking if you are
sure you want to remove the ADK.

Click OK to remove the ADK. The ADK is removed.

Managing PGP Keys
Working with Revokers

Working with Revokers
It is possible that one day you might forget your passphrase or lose your keypair (your
laptop is stolen or your hard drive crashes, for example).
Unless you are also using Key Reconstruction and can reconstruct your private key, you
would be unable to use your key again, and you would have no way of revoking it to
show others not to encrypt to it. To safeguard against this possibility, you can appoint a
third-party key revoker. The third-party you designate is then able to revoke your key
just as if you had revoked it yourself.
This feature is available for both Diffie-Hellman/DSS and RSA keys.
You can only change revoker information on your keypairs. If a public key on your
keyring has a revoker, you can see that information but you cannot change it.

Appointing a Designated Revoker
To add a designated revoker to your key
1

Open PGP Desktop, then select My Private Keys, under the Keys item. All of the
keys on your keyring appear.

Double-click the key to which you are adding a revoker. The Key Info dialog box
for the key you selected is displayed.

Click the plus sign icon on the right side of the Revokers section. The Select key(s)
dialog box is displayed.

Select the key you want to use as the revoker key, then click OK. A PGP Warning
dialog box is displayed, asking if you are certain that you want to grant revoker
privileges to the selected key(s).

Click Yes to continue or No to cancel. The Enter PGP Passphrase for Key dialog
box is displayed.

Enter the passphrase for the keypair to which you are adding the revoker, then
click OK. A PGP Information dialog box is displayed.

Click OK. The selected key(s) is now authorized to revoke your key. For effective
key management, distribute a current copy of your key to the revoker(s) or upload
your key to the keyserver.

Revoking a Key
If the situation ever arises that you no longer trust your personal keypair, you can
revoke your key, which tells everyone to stop using your public key.
The best way to circulate a revoked key is to place it on a public keyserver.

Managing PGP Keys
Splitting and Rejoining Keys

To revoke a key
1

Open PGP Desktop, then select My Private Keys under the Keys item. All of the
keys on your keyring appear.

Ctrl+click the key you want to revoke (or right-click if you are using a two-button
mouse).

In the shortcut menu, select Revoke. A Confirm Revocation dialog box is
displayed, asking if you are sure you want to revoke this key.

Click OK to confirm your intent to revoke the selected key or Cancel to cancel.

Enter the passphrase for the keypair you are revoking, then click OK. When you
revoke a key, it is marked out with a red X to indicate that it is no longer valid.

Synchronize the revoked key so everyone will know not to use the now revoked
public key.

Splitting and Rejoining Keys
Any private key can be split into shares among multiple “shareholders” using a
cryptographic process known as Blakely-Shamir key splitting. This technique is
recommended for extremely high security keys.
For example, Symantec Corporation keeps a corporate key split between multiple
individuals. Whenever we need to sign with that key, the shares of the key are rejoined
temporarily.

Creating a Split Key
When you split a key, the shares are saved as files either encrypted to the public key of
a shareholder or encrypted conventionally if the shareholder has no public key. After
the key has been split, any attempts to sign or decrypt with it will automatically
attempt to rejoin the key.
To create a split key
1

Open PGP Desktop, then click the PGP Keys item. All of the keys on your keyring
appear.

Select the keypair you want to split. The selected keypair highlights.

Select Keys > Share Key > Make Shared. The Split Key dialog box is displayed.

Add shareholders for the split key by dragging and dropping their keys in the
Key/User Name list.

To add a shareholder who does not have a public key, that person must be
physically present to enter their own passphrase. Click Add.
•

Allow the shareholder to type in their passphrase twice, then click OK.
Unnamed User is displayed in the list.

•

Double-click Unnamed User and enter a descriptive name for the person or
organization holding the shares.

Managing PGP Keys
Splitting and Rejoining Keys

To specify a location for the split shares, click Browse in the Share File
Destination Folder, then select the desired location.

When all of the shareholders are listed, you can specify the number of key shares
that are necessary to decrypt or sign with this key.
By default, each shareholder is responsible for one share. To increase the number
of shares a shareholder possesses, double-click the number in the Shares column
and enter the number of shares they control.

Click Split Key. The Confirm Key Split dialog box is displayed.

Click OK to continue splitting the key. The Passphrase screen is displayed.

Enter the passphrase for the key being split, then click OK. A minimum of six
characters is required for this passphrase. A confirmation dialog box opens.
The key is split and the shares are saved in the location you specified. Each key
share is saved with the shareholder’s name as the file name and a .shf extension.

Distribute the key shares to the owners, then delete the local copies of the shares.

Be sure you keep the original key that was split. You will need to have this key before
you can rejoin the split key for any decryption functions.

Rejoining Split Keys
Once a key is split among multiple shareholders, attempting to sign or decrypt with it
causes PGP Desktop to attempt to rejoin the key automatically. There are two ways to
rejoin the key: locally and remotely.
Rejoining key shares locally requires the shareholder’s presence at the rejoining
computer. Each shareholder is required to enter the passphrase for their key share.
Rejoining key shares remotely requires the remote shareholders to authenticate and
decrypt their keys before sending them over the network. The PGP Desktop Transport
Layer Security (TLS) feature provides a secure link to transmit key shares, allowing
multiple individuals in distant locations to securely sign or decrypt with their key
share.
Caution: Before receiving key shares over the network, you should verify each
shareholder’s fingerprint and sign their public key to ensure that their
authenticating key is legitimate.
Before you begin, be sure you have the original key that was split on the rejoining
computer.
To rejoin a split key
1

Contact each shareholder of the split key. To rejoin key shares locally, the
shareholders of the key must be present.
To collect key shares over the network, make sure the remote shareholders have
PGP Desktop installed and are prepared to send their key share file. Remote
shareholders must have:
•

Their key share files and passwords.

•

A keypair (for authentication to the computer that is collecting the key
shares).

•

A network connection.

Managing PGP Keys
If You Lost Your Key or Passphrase

•

The IP address or Fully Qualified Domain Name of the computer that is
collecting the key shares.

At the rejoining computer, use the Finder to select the file(s) that you want to sign
or decrypt with the split key.

Ctrl+click the file(s) and select Sign or Decrypt from the PGP shortcut menu. The
Enter PGP Passphrase for Selected Key screen is displayed with the split key
selected.

Click OK to reconstitute the selected key. The Key Share Collection screen is
displayed.

Do one of the following:
•

If you are collecting the key shares locally, click Select Share File and then
locate the share files associated with the split key. The share files can be
collected from the hard drive, a removable drive, or a mounted drive.
Continue with the next step.

•

If you are collecting key shares over the network, click Start Network.
The Passphrase dialog box opens. In the Signing Key field, select the keypair
that you want to use for authentication to the remote system and enter the
passphrase. Click OK to prepare the computer to receive the key shares.
The status of the transaction is displayed in the Network Shares box. When
the status changes to Listening, the PGP application is ready to receive the key
shares.
At this time, the shareholders must send their key shares.
When a share is received, the Remote Authentication screen is displayed. If
you have not signed the key that is being used to authenticate the remote
system, the key will be considered invalid. Although you can rejoin the split
key with an invalid authenticating key, it is not recommended. You should
verify each shareholder’s fingerprint and sign each shareholder’s public key to
ensure that the authenticating key is legitimate.

Click Confirm to accept the share file.

Continue collecting key shares until the value for Total Shares Collected matches
the value for Total Shares Needed on the Key Shares Collection screen.

Click OK. The file is signed or decrypted with the split key.

If You Lost Your Key or Passphrase
If you lost your key, you can reconstruct your key so you can continue to encrypt and
decrypt data. How you do this depends on if you are using PGP Desktop in a standalone
environment or in a PGP Universal Server-managed environment.
If you forgot your passphrase, you can reset your passphrase. To do this, you answer
correctly three of the five security questions you answered when you set up your key or
created your security questions.

Managing PGP Keys
If You Lost Your Key or Passphrase

Reconstructing Keys with PGP Universal Server
This section applies only to PGP Desktop users in a PGP Universal Server-managed
environment whose PGP administrator has configured key reconstruction support
for their copy of PGP Desktop.
If you lose your key or forget your passphrase and do not have a backed up copy from
which to restore your key, you will never again be able to decrypt any information
encrypted to your key. You can, however, reconstruct your key if your PGP
administrator has implemented a PGP key reconstruction policy for you, in which your
key is encrypted and stored on a PGP Universal Server in such a way that only you can
retrieve it.
The PGP Universal Server holding the key reconstruction data stores your key in such a
way that only you can access it. Not even the PGP administrator has the ability to
decrypt your key.
If your PGP administrator has configured support for key reconstruction, you will be
prompted to enter additional “secret” information when you install PGP Desktop or
when you create your security questions.
Once your key is on the server, you can restore it at anytime by selecting Keys > I Lost
My Key or Keys > I Forgot My Passphrase in PGP Desktop for Windows, or Keys >
Reconstruct in PGP Desktop for Mac OS X.
Tip: If you were not prompted to create your PGP questions during installation of
PGP Desktop, and your PGP Universal Server administrator allows local key
reconstruction, you can manually create your questions. For more information, see
Creating Your Security Questions (on page 70).

Creating Key Reconstruction Data
When you answer the PGP security questions, you are creating the key reconstruction
data. In a standalone environment, this information is stored on your local disk in a .krb
file. In a managed environment, you send the key reconstruction data to your
company's PGP Universal Server whenever you install PGP Desktop or when you reset
your key.
Choose obscure personal questions with answers that you are not likely to forget. Your
questions can be up to 95 characters in length. An example of a good question might be,
“Who took me to the beach?” or “Why did Fred leave?” An example of a bad question
would be, “What is my mother’s maiden name?” or “Where did I go to high school?”
When you have created and answered all five PGP questions, your private key is split
into five pieces, using Blakely-Shamir key splitting. Three of the five pieces are needed
to reconstruct the key. Each piece is then encrypted with the hash, the uniquely
identifying number, of one answer. If you know any three answers, you can successfully
reconstruct the whole key.

Creating Your Security Questions
Before you can reconstruct your key or create a new passphrase when you've forgotten
it, you must create your security questions. You can customize the five security
questions so that the answers are something that only you would know.

Managing PGP Keys
If You Lost Your Key or Passphrase

To create your security questions
1

In PGP Desktop, click the Keys item and then select your key.

Select Keys > Create My PGP Questions. The PGP Security Question Assistant is
displayed.

When the Key Reconstruction screen dialog box is displayed, type five questions
that only you can answer in the Question fields (the default questions are
examples only).

In the first Create Security Question screen, click the arrow for the first field to
select the question you want to use. Note that you can customize parts of the
question in the next step.
If you want to completely customize the question to create your own question,
select Enter my own question.

For Personalize Your Question, click the arrows next to any of the text that you
can customize. For example, if you selected the first question, you can customize
that question by changing "friend" to "boy" and "had a crush on" to "held hands
with."
If you chose to create your own question, enter the question in this field. Be sure to
enter a question that only you can know the answer to.

For Answer Your Question, enter the answer to this security question. You can
enter the answer using mixed upper- and lowercase letters, or use all one case
(when you answer the question, the case will not matter).
A hint is displayed in this field that disappears once you start entering the answer.
For example, to answer the question "Who was the first boy that I ever held hands
with?", the hint is "Enter first and last name".

When you have defined your question and entered the answer, click Next to
continue. The Create Security Question 2 of 5 dialog box is displayed.

You are prompted to create and answer a total of five security questions. Continue
to follow the steps above to select the question, customize the question, and
answer the question.

Managing PGP Keys
If You Lost Your Key or Passphrase

When you have entered all five questions and answers, the Enter PGP Passphrase
dialog box is displayed.

Enter the passphrase for your key and click OK.

You are then prompted to save the key reconstruction file. Enter the name and
location where you want to save the file and click Save.

Click Finish to exit the assistant.

You have now defined the five security questions. If you lost your key or forget your
passphrase, you can reconstruct your key or reset your passphrase by answering three
of these five questions.

Reconstructing Your Key if You Lost Your Key or Passphrase
If you have lost your key or have forgotten your passphrase, you can recover by
reconstructing your key. You must first have created a set of security questions that
only you can answer. For more information, see Creating Your Security Questions (on
page 70).
To reconstruct your key
1

In PGP Desktop, click the Keys item and then select your key.

Select Keys > Reconstruct.
•

If you are managed by a PGP Universal Server, the PGP Passphrase
Assistant: Answer Security Questions dialog box is displayed.

•

If you are in a standalone environment, the Select Key Reconstruction File
dialog box is displayed. Select the .krb file that you saved when you created
your security questions and click Open.

The Key Reconstruction dialog box is displayed.

Answer three of the five security questions correctly and click Continue. The
Confirm PGP Passphrase dialog box is displayed.

Managing PGP Keys
Protecting Your Keys

Enter and re-enter your new passphrase.
Select Show Keystrokes if you want to see the characters you type for your
passphrase. Be sure no one can see what you type.
The Passphrase Quality bar provides a basic guideline for the strength of the
passphrase you are creating by comparing the amount of entropy in the
passphrase you type against a true 128-bit random string (the same amount of
entropy in an AES128 key). For more information, see The Passphrase Quality Bar
(on page 180).

Click OK. Your key has been reconstructed.

Protecting Your Keys
Besides making backup copies of your keys, you should be especially careful about
where you store your private key. Even though your private key is protected by a
passphrase that only you should know, it is possible that someone could discover your
passphrase and then use your private key to decipher your email or forge your digital
signature. For instance, somebody could look over your shoulder and watch the
keystrokes you enter or intercept them on the network or even over the Internet.
To prevent anyone who might happen to intercept your passphrase from using your
private key, store your private key only on your own computer. If your computer is
attached to a network, make sure that your files are not automatically included in a
system-wide backup where others might gain access to your private key. Given the ease
with which computers are accessible over networks, if you are working with extremely
sensitive information, you may want to keep your private key on a flash drive, which
you can insert like an old-fashioned key whenever you want to read or sign private
information.
As another security precaution, consider assigning a different name to your private
keyring file and then storing it somewhere other than in the default location.
Your private and public keys are stored in separate keyring files. You can copy them to
another location on your hard drive or to a diskette. By default, the private keyring
(secring.skr) and the public keyring (pubring.pkr) are stored along with the other
program files in your “PGP” folder; you can save your backups in any location you like.
You can configure PGP Desktop to back up your keyrings automatically after you close
PGP Desktop. Your keyring backup options can be set in the Keys tab of the Options
dialog box (for Windows systems) or the Preferences dialog box (for Mac OS X systems).
Tip: If you have changed your passphrase on your key, remember that it does not
change the passphrase on any copies of the key (such as backups you may have
made). If you think your key has been compromised, PGP recommends that you
shred any previous backup copies and then make new backups of your key.

Securing Email Messages

This section describes how to use PGP Desktop Email to automatically and
transparently secure your email messages.
Note: If you are using PGP Desktop in a PGP Universal Server-managed
environment, your PGP Universal Server administrator may have disabled certain
features. When a feature is disabled, the control item in the left side is not displayed
and the menu and other options for that feature are not available. The graphics
included in this guide depict the default installation with all features enabled. If your
PGP Universal Server administrator has disabled this functionality, this section does
not apply to you.

In This Chapter
How PGP Desktop Secures Email Messages ..............................................................75
Using Offline Policy ......................................................................................................78
Services and Policies.....................................................................................................79
Creating a New Security Policy ...................................................................................86
Working with the Security Policy List .......................................................................95
PGP Desktop and SSL..................................................................................................100
Key Modes.....................................................................................................................101
Viewing the PGP Log...................................................................................................103
Using PGP Scripts with Entourage 2008 .................................................................104

How PGP Desktop Secures Email Messages
When secure email messaging is enabled, PGP Desktop monitors the email traffic
between your email client and your mail server. Depending on the circumstances, PGP
Desktop will intercede on your behalf to encrypt, sign, decrypt, or verify messages.
Once configured correctly—and it’s very likely PGP Desktop can do that for you
automatically—you don’t have to do anything to encrypt and/or sign outgoing messages
or to decrypt and/or verify incoming messages; the PGP Desktop messaging proxy does
it for you.
How this happens is different for incoming and outgoing messages.
For incoming messages, PGP Desktop automatically evaluates all incoming email
messages and takes the appropriate actions (described in the following section).

Securing Email Messages
How PGP Desktop Secures Email Messages

For outgoing messages, there are a range of actions that PGP Desktop can take on your
behalf based on configured policies. A policy is a set of instructions (such as "In this
circumstance, do this") that tells PGP Desktop what to do in specific situations. By
combining these instructions, policies can be tailored to meet all of your email security
requirements. PGP Desktop comes pre-configured with a set of policies that suit the
needs of the vast majority of users. However, you are also provided with fine-grained
control over these policies if you want to change them.
By default, when you are using PGP Desktop standalone and are sending an outgoing
message, PGP Desktop looks for a key it can trust to encrypt the message. It looks first
on the default keyring (called "All Keys" on Windows systems) or the local keyring
(called "Keys" on Mac OS X systems) for the public key of the recipient. If it does not
find such a key, it will, again by default, check the PGP Global Directory for a trusted
key for the recipient. If it does not find a trusted key there, the message is sent in the
clear, which is unencrypted. This default behavior, called Opportunistic Encryption,
strikes a balance between protecting outgoing messages and making sure they get sent.
Creating new policies is covered in detail in Creating a New Security Policy (on page 86).
If you are in a PGP Universal-protected domain, your local PGP Desktop policies
determine how your messages are encrypted and when. For more information, consult
with your organization’s PGP Universal Server administrator.

Incoming Messages
PGP Desktop manages incoming mail messages based on the content of the message.
These scenarios assume standalone PGP Desktop, not in a domain protected by a PGP
Universal server (in which case mail action policies set by your PGP Universal Server
administrator can apply):
•

Message not encrypted nor signed. PGP Desktop does nothing to the content of
these messages; it simply passes the message along to your email client.

•

Message encrypted, but not signed. When PGP Desktop sees a message coming to
you that is encrypted, it will attempt to decrypt it for you. To do this, PGP Desktop
will check the local keyring for the private key that can decrypt the message. If the
private key is not on the local keyring, PGP Desktop will not be able to decrypt it;
the message will be passed to your email client still encrypted. If the private key is
on the local keyring, PGP Desktop will decrypt it immediately if the passphrase for
the private key is in memory (cached). If the passphrase is not cached, PGP
Desktop will prompt you for the passphrase and decrypt the message when you
supply the correct passphrase. Once a message is decrypted, PGP Desktop passes it
to your email client.
If the PGP Desktop messaging proxy is turned off, PGP Desktop will not be able to
decrypt incoming encrypted messages; it will pass them along to your email client
still encrypted. It is recommended that you leave your messaging proxy on all the
time if you expect to be sending and receiving encrypted messages. On is the
default setting.

Securing Email Messages
How PGP Desktop Secures Email Messages

•

Message signed, but not encrypted. PGP Desktop will search the local keyring for
a public key that can be used to verify the signature. If PGP Desktop cannot find
the appropriate public key on the local keyring, it will try to search for a keyserver
at keys.domain (where domain is the domain of the sender of the message), then
the PGP Global Directory (https://keyserver.pgp.com), and finally any other
configured keyservers. If PGP Desktop finds the right public key at any of these
locations, it verifies the signature (or not, if the signature is bad) and passes the
message to your email client annotated with information about the
signature—information is also put into the PGP Log. If PGP Desktop cannot find
the appropriate public key, it passes the message to your email client unverified.

•

Message encrypted and signed. PGP Desktop goes through both of the processes
described above: first finding the private key to decrypt the message and then
finding the public key to verify the signature. However, if a message cannot be
decrypted, then it cannot be verified.

If PGP Desktop is unable to either decrypt or verify a message, you might want to
consider contacting the sender of the message. If the message could not be decrypted,
make sure the sender was using your real public key. If the message could not be
verified, ask the sender to publish their key on the PGP Global Directory — older PGP
versions or other OpenPGP products can access the web version of this directory at PGP
Global Directory (https://keyserver.pgp.com) , or ask them to send their public key to you
directly by email.
Note: PGP Desktop only encrypts by default to keys that are known to be valid. If you
did not get a key from the PGP Global Directory, you may need to verify its
fingerprint with the owner and sign it for it to be used.

Understanding Annotations on Incoming Messages
When incoming email messages are received, PGP Desktop decrypts any encrypted
portions and verifies any signatures. Then a snippet of text, called an annotation, is
inserted into the processed email message to indicate what encryption and signatures
were present. Any email message with at least partial protection (encrypted, signed, or
both) receives an annotation. If an email message is completely unprotected (for
example, the email is not encrypted or signed by the sender) then the message is not
annotated.
You can choose three annotation levels:
•

Maximum: Verbose Annotation. Adds annotations to your incoming email
detailing every action that PGP Desktop has taken during message processing.

•

Medium: Failures and Successes. This option is the default. Provides annotations
when there has been a processing failure, such as unknown key, or unknown
signer. The Medium setting provides annotations for all decrypted and/or signed
email, but does not list individual attached files.

•

Minimum: Failures Only. Only provides annotations when there has been a
processing failure, such as detecting an unknown key or unknown signer.

To specify the level of annotation you want to use, see Messaging Options (see
"Messaging Preferences" on page 170).
In a PGP Universal Server-managed environment, your administrator may have
specified the location of the annotation. The annotation can be "wrapped around" the
message text (the default setting), or placed below the message text.

Securing Email Messages
Using Offline Policy

For more information on annotations, see PGP KB article 2039
(http://support.pgp.com/?faq=2039).

Outgoing Messages
Email messages that you send can be encrypted, signed, both, or neither. Because you
probably have different combinations for different recipients or email domains, you
need to create policies for all of your outgoing email message possibilities. Once correct
policies are in place, your email messages are protected automatically and
transparently.
If you are in a PGP Universal Server-managed environment, your PGP Desktop policies
are controlled by the policies specified by your PGP Universal Server administrator.
Your administrator may also have specified how to handle outgoing email messages if
the PGP Universal Server is not available. These policies are called offline (or local)
policies.

Securing Sent Items on IMAP Email Servers
If you are using an IMAP email server, messages in your Sent Items folder are typically
stored on the mail server. IMAP email clients send the sent message copy over the
network to the folder using the IMAP protocol. If the sent message is not encrypted, the
message could be intercepted. PGP Desktop provides the ability for sent messages to be
encrypted and/or signed as they are sent to the IMAP server.
In a PGP Universal Server-managed environment, your administrator may have
specified that all messages in the Sent Items folder be secured.
In a standalone environment, you can specify if you want to secure the sent messages.
To do this, choose Tools > Options (in PGP Desktop for Windows) or PGP > Preferences
(in PGP Desktop for Mac OS X) and click the Messaging tab or item. Then specify if you
want to encrypt, encrypt and sign, or just sign the messages.
Email messages are encrypted using your public PGP key.
When you access your Sent Items folder, and your key's passphrase is not cached, you
are prompted to enter the passphrase.
If the name of the folder is not a name that PGP Desktop recognizes (for example,
instead of "Sent Items" the folder is named "Outgoing Messages"), a message is
displayed asking you confirm if the name of the folder is where your sent messages are
typically stored. Note that the first message copied to this folder is not encrypted
and/or signed, but that subsequent messages copied to this folder are.

Using Offline Policy
If you are using PGP Desktop in a PGP Universal Server-managed environment, the
offline mail policy is defined by your PGP Universal Server administrator. This policy
defines what happens to email messages when the PGP Universal Server is offline or
cannot be reached by PGP Desktop.

Securing Email Messages
Services and Policies

•

Block outbound messages. Your outbound messages are not sent. If the messages
can be queued by your mail client, they stay in the queue until the PGP Universal
Server is available. If the messages cannot be queued, the email messages are
blocked.

•

Send outbound messages in the clear. You are prompted to choose if you want to
allow the email message to be sent unsecured. If you choose to send, the message
is sent in the clear. If you choose not to send, the message is blocked.

•

Follow standalone policy. PGP Desktop follows the standalone policy to process
your outbound messages. For more information, see Viewing Services and Policies
(on page 80).

For information on the notifiers you receive when any of the above occurs, see Outgoing
PGP Desktop Notifier Messages for Offline Policy (on page 29).
Your PGP Universal Server administrator can specify how often your mail policies get
downloaded to PGP Desktop. When you are in offline mode, the last downloaded offline
mail policy remains in effect for processing your outbound email messages. If you have
been in offline mode for a period of time that is longer than the grace period allowed for
the offline standalone mail policy to be in effect, your administrator could have also
specified how outgoing email should be processed. In this case, PGP Desktop can start
blocking your outbound messages or the same offline standalone mail policy can be
used for processing your outbound messages, depending on how policy is defined by
your administrator.
When you have been offline for some time, you can manually request a download of
policy from the PGP Universal Server once you are back online. To do this when you are
back online, select the PGP Desktop icon in the tray and then select Update Policy. The
latest policies are downloaded from the PGP Universal Server and any client logs are
uploaded to the server. The option to manually update a policy is available for managed
users only.
If your PGP Universal Server administrator allows you to use standalone policies, see
Creating a New Security Policy (on page 86).

Services and Policies
To understand how to use PGP Desktop to automatically and transparently protect your
outgoing messages, you need to understand two terms: service and policy.
•

Service. Information about one email account on your system and the policies that
apply to that account. In most cases, PGP Desktop will automatically create and
configure a service for each email account on your system. In some circumstances,
you may want to create and configure a service manually.

•

Policy. A set of one or more instructions that tell PGP Desktop what to do in
specific situations. Policies are associated with services—often more than one (a
policy can be reused by different services). Conversely, a service can (and usually
does) have more than one policy.

When deciding how to handle a specific outgoing email message, PGP Desktop checks
the policies configured for the service one at a time (from the top of the list going
down). When it finds a policy that applies, it stops checking policies and implements
the one that applies.
All new services are created with the following default policies:

Securing Email Messages
Services and Policies

•

Encrypt and Sign Buttons. Specifies that email is both signed and encrypted when
both the Encrypt and Sign buttons are enabled in Microsoft Outlook 2002, 2003,
or 2007. This policy is available only on PGP Desktop for Windows.

•

Sign Button. Specifies that email is signed when the Sign button is enabled in
Microsoft Outlook 2002, 2003, or 2007. This policy is available only on PGP
Desktop for Windows.

•

Encrypt Button. Specifies that email is encrypted when the Encrypt button is
enabled in Microsoft Outlook 2002, 2003, or 2007. This policy is available only on
PGP Desktop for Windows.

•

Mailing List Admin Requests. Specifies that administrative requests to mailing
lists are sent in the clear; that is, not encrypted or signed.

•

Mail List Submissions. Specifies that submissions to mailing lists are sent signed
(so they can be authenticated) but not encrypted.

•

Require Encryption: [PGP] Confidential. Specifies that any message flagged as
confidential in your email client or containing the text “[PGP]” in the subject line
must be encrypted to a valid recipient public key or it cannot be sent.

•

Opportunistic Encryption. Specifies that any message for which a key to encrypt
cannot be found should be sent without encryption (in the clear). Having this
policy as the last policy in the list ensures that your messages will always be sent,
albeit in the clear, even if a key to encrypt it to the recipient cannot be found.
Do not put Opportunistic Encryption first in the list of policies (or anywhere but
last, for that matter) because when PGP Desktop finds a policy that matches, and
Opportunistic Encryption matches everything, it stops searching and implements
the matching policy. So if a policy is lower on the list than Opportunistic
Encryption, it will never be implemented.
Note: The default policies can be modified, but not deleted. Alternatively, they can be
disabled, then moved up or down in the list of policies.

Viewing Services and Policies
To view services and policies
1

Open PGP Desktop and click the PGP Messaging item.

Click the name of the service whose account properties you want to view. The
settings for the selected service appear in the PGP Messaging Work area.

Securing Email Messages
Services and Policies

To view the details of a policy, under Security Policies, click the name of the
policy you want to view and click View Policy. The settings for the policy are
displayed. This section provides information on what security policy is being
enforced. If you are managed by a PGP Universal Server, the security policies are
set by your administrator.

If you are using PGP Desktop in a PGP Universal Server-managed environment, you
may have the option to override server policies with local policies. If specified by policy,
your local policies may be enforced if your PGP Universal Server becomes unavailable
for any reason.

Creating a New Messaging Service
A service is information about an email account, as well as the security policies that are
to be applied to outgoing messages for that email account.
Important: In most cases, PGP Desktop creates services for you as you use your email
accounts to send or receive messages. If you need to create a service yourself, make
sure to read and understand these instructions. Incorrect configuration of a service
could result in problems sending or receiving email messages.
To create a new service
1

Open PGP Desktop and click the PGP Messaging item. The PGP Messaging screen
is displayed.

Click Create New Service. Or, from the Messaging menu, select New Service. The
New Service screen is displayed. The Service Properties section shows default
settings and the Security Policies section displays default security policies.

In the Description field, enter a descriptive name for this service. (This step is
optional, but helpful when you work with multiple services).

Securing Email Messages
Services and Policies

In the Email Address field, enter the email address associated with this service
(for example, acameron@example.com).

Type the name of your incoming and outgoing email servers, or click Server
Settings if you want to set advanced options.

If you chose to set advanced options, the Server Settings dialog box is displayed.
Enter the appropriate settings:
•

Server Type: Select the type of server that the new service will be using:
PGP Universal Server—for PGP Desktop users who are in a PGP Universal
Server-managed environment. Contact your PGP administrator for more
details on correct settings. If you are using PGP Desktop in a PGP Universal
Server-managed environment, the correct settings for the Server Settings
dialog box were automatically downloaded.
Internet Mail—for standalone PGP Desktop users who have a POP or IMAP
mail connections.

•

Name: Enter the name of the mail server that handles incoming messages.

•

Protocol: Select the protocol used to pick up messages on the incoming mail
server. The Automatic setting can automatically detect either POP or IMAP
connections.

•

Port: Keep Automatic (the default) or specify a port to connect to on the
incoming mail server to pick up messages (if you have selected either the
Internet Mail or PGP Universal settings and either POP or IMAP—not
Automatic).

•

SSL/TLS: Specify how PGP Desktop interacts with your mail server:

•

Automatic: PGP will do its best to provide SSL/TLS protection. It first tries
the alternate port, then it attempts STARTTLS (if supported by the server),
finally, if the above fails, it connects to the server unprotected.

•

Require STARTTLS: PGP Desktop requires the server honor the STARTTLS
command.

•

Require SSL: PGP Desktop requires that the server honor SSL-protected
connections on the specified alternate port.

•

Do Not Attempt: PGP Desktop does not attempt any SSL/TLS protection of
the connection with the mail server.

•

Warn if email client attempts SSL/TLS: When selected, PGP Desktop
displays a warning dialog if the email client attempts SSL/TLS, as this is a
condition that is incompatible with PGP Desktop proxying your email. (This
option is selected by default.)

Caution: This option should be enabled only if you are certain your mail server
supports SSL. It ensures that PGP Desktop will not fall back to sending or
receiving messages with the mail server over an unprotected connection if, for
example, a problem occurs while negotiating SSL protection for the connection.
If you enable this option and your mail server does not support SSL, PGP
Desktop will not send or receive any of your messages.
•

Name: Enter the name of the mail server that handles outgoing messages.

•

Port: Keep Automatic (465, 25) or specify another port to connect to on the
outgoing mail server to send messages. This option is available only for the
outgoing mail server if your settings permitted choosing it for the incoming
mail server.

Securing Email Messages
Services and Policies

•

SSL/TLS: Specify how PGP Desktop interacts with your mail server:
Automatic: PGP will do its best to provide SSL/TLS protection. It first tries the
alternate port, then it attempts STARTTLS (if supported by the server), finally,
if the above fails, it connects to the server unprotected.
Require STARTTLS: PGP Desktop requires that the server honor the
STARTTLS command.
Require SSL: PGP Desktop requires that the server honor SSL-protected
connections on the specified alternate port.
Do Not Attempt: PGP Desktop does not attempt any SSL/TLS protection of the
connection with the mail server.

•

Note: If you are manually connecting to a PGP Universal Server, see Manually
binding to a PGP Universal Server (on page 187).

Editing Message Service Properties
Caution: Before making any changes to an existing messaging service, be sure to exit
your email client.
To make changes to the account properties of an existing service
1

Open PGP Desktop and click the PGP Messaging item.
Click on the name of the service whose account properties you want to edit. The
settings for the selected service appear in the PGP Messaging Work area.

Make the desired changes to the account properties of the service. For more
information, see Creating a New Messaging Service (on page 81).

Disabling or Enabling a Service
If you want to stop a service from working, but you don’t want to delete the service
because you might need it again, you can disable the service. This is useful if you only
want PGP Desktop to process mail on particular accounts, but not others. If you are
certain that you won’t need the service again, you can delete the service (see "Deleting a
Service" on page 84).
To enable or disable an existing service
1

Under the PGP Messaging item, select the name of the service you want to disable.
The settings for the service appear. Confirm that you have selected the correct
service.

Do one of the following:

Securing Email Messages
Services and Policies

•

To disable the service, select Messaging > Disable Service. The service is
disabled.

•

To enable the service select Messaging > Enable Service. The service is
enabled.

Tip: You can also Ctrl+click the name of the service (or right-click it if you are
using a two-button mouse) and select the option to enable or disable the service
from the shortcut menu.

Deleting a Service
If you are certain that you will not need a messaging service any longer, you can delete
the service from PGP Desktop.
To delete a service
1

Under the PGP Messaging item, select the name of the service you want to enable.
The settings for the service appear. Confirm that you have selected the correct
service.

Ctrl+click the name of the service (or right-click it if you are using a two-button
mouse) and select Remove Item from the shortcut menu. The service is deleted.

Multiple Services
Some email services and Internet Service Providers use multiple mail servers for a
single DNS name in a round-robin fashion such that PGP Desktop may create multiple
messaging services for a single email account, seeing each mail server as separate and
thus requiring its own messaging service.
PGP Desktop ships with wildcard support for common email services, such as
*.yahoo.com and *.me.com (or *.mac.com). However, if you are using a less-common
email service or if the services change their mail server configurations, you could run
into this problem.
If you see PGP Desktop create multiple services for a single email account, and you
check the settings and see they are the same except the mail server for the first service
is mail1.example.com, the mail server for the second service is
mail2.example.com, and the mail server for the third is mail3.example.com, and
so on, you may need to manually edit one of the services.
The best solution is to manually edit one of the services such that the mail server entry
for that service can support multiple mail servers being used round-robin. For the
example cited above, you could manually change the server name on the Server
Settings dialog box for one of the services to mail*.example.com, and then delete the
other services.
Some round-robin setups may be more complicated, requiring a slightly different
solution. For example, if PGP Desktop were to create services with mail servers of
pop.frodo.example.com, smtp.bilbo.example.com, and mail.example.com, then the best
wildcard solution would be *.example.com.

Securing Email Messages
Services and Policies

Troubleshooting PGP Messaging Services
By default, PGP Desktop automatically determines your email account settings and
creates a PGP Messaging service that proxies messaging for that email account.
Because of the large number of possible email account settings and mail server
configurations, on some occasions a messaging service that PGP Desktop automatically
creates may not work quite right.
If PGP Desktop has created a messaging service that is not working right for you, one or
more of the following items may help correct the problem:
•

Verify that you can both connect to the Internet and send and receive email with
PGP Services stopped. To do this:
•

On Windows systems, right-click the PGP Desktop tray icon and select Stop
PGP Services from the list of commands.

•

On Mac OS X systems, hold down the Option key and select Quit from the
PGP Desktop icon in the Menu bar.

Note: You should always restart your email client after starting or stopping PGP
Services.
•

Read the PGP Desktop Release Notes for the version of PGP Desktop you are using
to see if your problem is a known issue.

•

Make sure SMTP authentication is enabled for the email account (in your email
client). This is recommended for PGP Desktop to proxy your messaging. If you
only have one email account and you are not using PGP Desktop in a PGP
Universal Server-managed environment, then SMTP authentication is not needed.
It is required when using a PGP Universal Server as your SMTP server, or when
you have multiple email accounts on the same SMTP server.

•

Open the PGP Log to see if the entries offer any clues as to what the problem
might be.

•

If SSL/TLS is enabled in your email client, you must disable it there if you want
PGP Desktop to proxy your messaging. (This does not leave the connection to and
from your mail server unprotected; by default PGP Desktop automatically
attempts to upgrade any unprotected connection to SSL/TLS protection. The mail
server must support SSL/TLS for the connection to be protected.)

•

If either Require STARTTLS or Require SSL is selected (in the SSL/TLS settings of
the Server Settings dialog box) your mail server must support SSL/TLS or PGP
Desktop will not send or receive any messages.

•

If your email account uses non-standard port numbers, make sure these are
included in the settings of your messaging service.

•

If PGP Desktop is creating multiple messaging services for one email account, use
a wild card for your mail server name. For more information, see Multiple Services
(on page 84).

•

Delete the PGP Messaging service that is not working correctly and send/receive
email. PGP Desktop regenerates the messaging service.

If none of these items help correct the problem, try the following:
1

Delete the PGP Messaging service that is not working correctly.

Securing Email Messages
Creating a New Security Policy

Stop all PGP Desktop services and then exit PGP Desktop if it was open. To stop
the services:
•

On Windows systems, right-click the PGP Desktop tray icon and select Exit
PGP Services from the list of commands.

•

On Mac OS X systems, hold down the Option key and elect Quit from the PGP
Desktop icon in the Menu bar.

Verify that you have Internet connectivity and can send and receive email with
PGP Messaging services stopped.

Open your email client and write down your email account settings (including user
name, email address, incoming and outgoing mail server, incoming mail server
protocol, and any non-standard mail server ports).

Close your email client and restart PGP Desktop, which restarts PGP services:
•

On Windows systems, either restart your computer or open PGP Desktop
from the Windows Start menu.

•

On Mac OS X systems, either restart your computer or open PGP Desktop.

Manually create a PGP Messaging service using the account settings you wrote
down.

Open your email client and begin sending and receiving messages.

If you continue to have problems with a PGP Messaging service, access any of the
following for assistance:
•

Symantec website (http://www.symantec.com)

•

PGP Support website (https://support.pgp.com)

•

PGP Support forums (http://forum.pgp.com)

Creating a New Security Policy
Security policies control how PGP Desktop handles outgoing email messages.
Note: When you create a new security policy, you are creating a messaging security
policy, not a mailing list policy. You cannot create a new mailing list policy, but you
can edit the default mailing list policies.
To create a new security policy
1

In the PGP Messaging item, click the name of the service for which you want to
create a new security policy. The settings for the service appear, including the list
of existing security policies.

Securing Email Messages
Creating a New Security Policy

Click the plus sign icon at the bottom of the screen. The Untitled Messaging Rule
dialog box is displayed.

If your email domain is protected by a PGP Universal Server, and you look at the
Message Policy settings for a policy from a PGP Universal Server, the fields may be
different from the fields shown above.
3

In the Description field, type a descriptive name for the policy you are creating.

In the First Section (stating the policy conditions), in the If field, select:

•

If any. The policy applies when any condition is met.

•

If all. The policy only applies when all conditions are met.

•

If none. The policy only applies if none of the conditions are met.

In the first condition field, select:
•

Recipient. The policy applies only to messages to the specified recipient.

•

Recipient Domain. The policy applies only to email messages in the
specified recipient domain.

•

Sender. The policy applies only to messages with the specified sender
address.

•

Message. The policy applies only to messages which have the specified
signed and/or encrypted state.

•

Message Subject. The policy applies only to messages with the specified
message subject.

•

Message Header. The policy applies only to messages for which the specified
header meets the specified criterion. Note that the conditions described in
the next section (is, is not, contains, and so on) apply to the text typed in the
text box that is displayed when you select Message Header.

Note: When searching message headers in MAPI email systems, you can search
on the Subject, Sensitivity, Priority, and Importance headers only.

Securing Email Messages
Creating a New Security Policy

•

Message Body. The policy applies only to messages with the specified
message body.

•

Message Size. The policy applies only to messages of the specified size (in
bytes).

•

Message Priority. The policy applies only to messages with the specified
message priority.

•

Message Sensitivity. The policy applies only to messages with the specified
message sensitivity.

In the second condition field, select:
•

is. The condition is met when text in the first condition field matches the text
typed in the text box.

•

is not. The condition is met when text in the first condition field does not
match the text typed in the text box.

•

contains. The condition is met when text in the first condition field contains
the text typed in the text box.

•

does not contain. The condition is met when text in the first condition field
does not contain the text typed in the text box.

•

begins with. The condition is met when text in the first condition field begins
with the text typed in the text box.

•

ends with. The condition is met when text in the first condition field ends
with the text typed in the text box.

•

matches pattern. The condition is met when text in the first condition field
matches the pattern typed in the text box.

•

greater than. The condition is met when message size is greater than the text
typed in the text box.

•

less than. The condition is met when message size is less than the text typed
in the text box.

In the third condition field, select:
•

text entry box. Type text for the matching criteria. For example, if you
selected Message Size is greater than, then type a number representing the
size of the message.

•

normal. Matching criteria for Message Sensitivity is normal.

•

none or normal. Matching criteria for Message Sensitivity is none (for Mac
OS X systems) or normal (for Windows systems).

•

personal. Matching criteria for Message Sensitivity is personal.

•

private. Matching criteria for Message Sensitivity is private.

•

confidential. Matching criteria for Message Sensitivity is confidential.

•

signed. Matching criteria for Message is signed.

•

encrypted. Matching criteria for Message is encrypted.

•

encrypted to key ID. Matching criteria for encrypted to key ID (you must
then type a key ID in the resulting text box).

•

low. Matching criteria for Message Priority is low.

•

normal. Matching criteria for Message Priority is normal.

Securing Email Messages
Creating a New Security Policy

•

high. Matching criteria for Message Priority is high.

Create more condition lines by clicking the plus sign icon.
8

In the Perform the following actions on the message section, in the first action
field, select:
•

Send In Clear. Specifies that the message should be sent in the clear; that is,
not signed nor encrypted.

•

Sign. Specifies that the message should be signed.

•

Encrypt to. Specifies that the message should be encrypted.

In the second action field, select:
•

recipient’s verified key. Ensures the message can be encrypted only to a
verified key of the intended recipient.

•

recipient’s unverified key. Allows the message to be encrypted to an
unverified key of the intended recipient. Will also encrypt to a verified key, if
available.

•

recipient’s verified end-to-end key. Ensures the message can be encrypted
only to a verified end-to-end key of the intended recipient. An end-to-end
key is a key in sole possession of the individual recipient. In a PGP Universal
Server-managed environment, this is a Client Key Mode key which is
different from a Server Key Mode key, where the PGP Universal Server is in
possession of the key.
Whether the key is end-to-end or not is shown in the Group field on the Key
Properties dialog box on Windows systems or the Key Info dialog box on Mac
OS X systems. No means that the key is end-to-end (is not part of a group), and
Yes means that it is not end-to-end.)

•

recipient’s unverified end-to-end key. Allows the message to be encrypted
to an unverified end-to-end key of the intended recipient. Will also encrypt
to a verified key, if available.

•

a list of keys. Specifies that the message can only be encrypted to keys on the
list.

Create more action lines by clicking the plus sign icon.
10

In the Prefer encoding field, select:
•

automatic. Lets PGP Desktop choose the message encoding format. This is
almost always the best option unless you know exactly why you need to use
one of the other message encoding formats explicitly.

•

PGP Partitioned. Sets PGP Partitioned as the preferred message encoding
format. This format is the most backwards compatible with older PGP and
OpenPGP products.

•

PGP/MIME. Sets PGP/MIME as the preferred message encoding format.
PGP/MIME is able to encrypt and sign the entire message including
attachments in one pass and is usually therefore faster and better able to
reproduce the full message fidelity.

•

S/MIME. Sets S/MIME as the preferred message encoding format. Choose
S/MIME if, for some reason, you need to force messages to be S/MIME even if
the user has a PGP key.

In the Recipient’s key is not available section (or in the If a recipient key cannot
be found section on Mac OS X systems), in the first Key Not Found field, select:

Securing Email Messages
Creating a New Security Policy

•

Search keys.domain and. Specifies a search that includes both keys.domain
as well as another server you specify.

•

Search. Allows for searching for an appropriate key if one is not found on
the local keyring.

•

Clear-sign message. Specifies that the message should be sent in the clear,
but signed.

•

Send message unsecured. Specifies that the message be sent in the clear.

•

Block message. Specifies that the message must not be sent if an appropriate
key is not found.

In the second Key Not Found field, select:
•

All keyservers. Allows all keyservers, including the PGP Global Directory, to
be searched for an appropriate key.

•

PGP Global Directory or keyserver.pgp.com. Specifies that only the PGP
Global Directory is searched.

•

[configured keyservers]. Specifies that only the keyserver you choose from
the list of currently configured keyservers is searched. Note that keyservers
other than the PGP Global Directory may provide unverified keys that
cannot be used if you require verified keys in the policy. Unless you know
exactly why you need to search another keyserver and are prepared to find
those keys manually to verify them when necessary, search only on the PGP
Global Directory. This option is available only on Windows systems.

•

Edit Keyserver List. Lets you add keyservers to the list of currently
configured keyservers. This option is available only on Windows systems.

In the last Key Not Found field, specify:
•

temporarily cache found keys. Specifies that a found key should be
temporarily saved in memory. Keys in this cache will automatically be used
when verifying signed messages, and will be used for encryption if they have
been verified.

•

ask to save found keys. Specifies that PGP Desktop should ask if you want to
save to your local keyring a particular found key.

•

save found keys. Specifies that found keys should automatically be saved to
your local keyring.

In the If no result field, select:
•

Clear-sign message. Allows messages for which an encryption key has not
been found to be signed and sent in the clear.

•

Send message unsecured. Do not encrypt message.

•

Block message. Prevents message for which an encryption key has not been
found from being sent.

Click OK when the policy settings are configured. The new policy is displayed in
the list of security policies.

Securing Email Messages
Creating a New Security Policy

Regular Expressions in Policies
PGP Desktop supports the use of regular expressions in security policies in text entry
boxes. Using regular expressions lets you match multiple text strings using a single text
string.
Note: In addition to the following examples, PGP Desktop also supports broader
regular expressions that adhere to standard formats. The “Matches Pattern” criteria
actually means “matches regular expression.”
Some mail policy rule conditions require that some part of an email must match a
pattern. The patterns in the condition take the form of a regular expression. A regular
expression is a string of characters that represents the format for a term to match. Any
term that fits the format of the regular expression is a match.
Some common elements of regular expressions:
?

indicates that there should be one or none of the previous expression

indicates that there is at least one of the previous expression

matches any single character

indicates that there should be none, one, or any number of the previous expression

[ ]

matches any single character contained within the brackets

[a-z]

matches any lowercase letter within the set from a to z

[1-9]

matches any digit within the set from 1 to 9

a sequence of exactly n matches of the
expression

{n}

The following are examples of regular expressions to match common items that may
appear in a sensitive email message.

Data

Example

Regular Expression

Phone number

(555)555-4567

\(?[2-9][0-9]{2}[\]-.)[2-9][0-9]{
2}[-.][0-9]{4}

Email address

joe@example.com

[a-zA-Z0-9._%-]+@[a-zA-Z0
9.-]+\.[a-zA-Z]{2,6}

Credit card number

1234 1234 1234 1234

[1-9][0-9]{3} ?[0-9]{4}
?[0-9]{4} ?[0-9]{4}

Social Security Number

123-45-6789

[0-9]{3}-[0-9]{2}-[0-9]{4}

City, state abbreviation

Palo Alto, CA

.*, [A-Z][A-Z]

2-character state
abbreviation

[A-Z][A-Z]

Zip code

12345

[0-9]{5}(-[0-9]{4})?

Dollar amounts, with leading
$3.95
$ symbol

\$[0-9]+.[0-9][0-9]

Date, numeric

[0-9]{4}-[0-9]{2}-[0-9]{2}

2003-08-06

Securing Email Messages
Creating a New Security Policy

Data

Example

Regular Expression

Date, alpha-numeric

Jan 3, 2003

(Jan|Feb|Mar|Apr|May|Jun|Jul
|Aug|Sep|Oct|Nov|Dec)\.?
(3[0-1]|[1-2][0-9]|0?[0-9]),
[0-9]{4}

HTTP URL

http://www.example.com

https?://(([012][0-9]{0,2}\.){3}
[012][0-9]{0,2}|([a-zA-Z0-9]+\
.)+[a-zA-Z0-9]{2,6})(/.*)?

IP address

123.123.123.123

([012][0-9]{0,2}\.){3}[012][0-9
]{0,2}

A blank line

Security Policy Information and Examples
When you create a service, several default security policies are automatically created:
•

Require Encryption: [PGP] Confidential

•

Sign + Encrypt Button*

•

Sign Button*

•

Encrypt Button*

•

Mailing List Admin Requests

•

Mailing List Submissions

•

Opportunistic Encryption.

* These policies are available only on PGP Desktop for Windows.
The order of the default policy rules is important. Be sure the order appears exactly as
described above.
This section describes how the default security policies work. It also describes two
example situations for which you might want to create a security policy and explains
how to configure them.
Note: If you make any changes to the default policies and want to restore the default
settings, click Revert to Default (for Windows systems) or Revert (for Mac OS X
systems) in the Message Policy dialog box.

Opportunistic Encryption Default Policy
Opportunistic Encryption is one of the default security policies that PGP Desktop
automatically creates for a service. The settings for this default policy are:
•

If: any

•

Conditions: Recipient Domain / is / *

•

Actions: Sign / Encrypt to / recipient’s verified key

•

Prefer message encoding: automatic

Securing Email Messages
Creating a New Security Policy

•

Key Not Found: Search keys.domain and / keyserver.pgp.com/ temporarily cache
found keys

If no result: Send message unsecured This rule should appear seventh (last) in the list of
default policies. Opportunistic Encryption causes those messages for which a verified
key can be found to be sent signed and encrypted. Those messages for which a verified
key cannot be found are delivered with no encryption (in the clear). This ensures your
messages get sent, although some may be sent in the clear.
This policy was designed to go last in your list of security policies, as it will match any
message sent. If placed above a policy in the list, PGP Desktop will never reach that
policy, thus rendering it useless.

Require Encryption: [PGP] Confidential Default Policy
Require Encryption: [PGP] Confidential is one of the default security policies that PGP
Desktop automatically creates for a service. The settings for this default policy are:
•

If: any

•

Conditions: Message Subject / contains / [PGP]
Message Sensitivity / is / confidential

•

Actions: Sign / Encrypt to / recipient’s verified key

•

Prefer message encoding: automatic

•

Key Not Found: Search keys.domain and / All Keyservers / temporarily cache
found keys

•

If no result: Block message

This rule should appear first in the list of policies.
Require Encryption: [PGP] Confidential causes those messages with subjects that
contain [PGP] or are marked confidential in your email client to require encryption to a
verified key in order to be sent. If a verified key cannot be found, the message is not
sent.

Mailing List Submission Default Policy
Mailing List Submission is one of the default security policies that PGP Desktop
automatically creates for a service.
The settings for this default policy are:
•

If: If any

•

Conditions: Recipient / matches pattern/ .*-users@.*, .*-bugs@.*, .*-docs@.*,
.*-help@.*, .*-news@.*, .*-digest@.*, .*-list@.*, .*-devel@.*, .*-announce@.*,

•

Actions: Sign

Prefer Encoding: PGP Partitioned This rule should appear sixth in the list of default
policies.

Securing Email Messages
Creating a New Security Policy

Mailing List Admin Requests Default Policy
Mailing List Admin Requests is one of the default security policies that PGP Desktop
automatically creates for a service.
The settings for this default policy are:
•

If: If any

•

Conditions: Recipient / matches pattern/ .*-subscribe@.*, .*-unsubscribe@.*,
.*-report@.*, .*-request@.*, .*-bounce@.*,

•

Actions: Send in clear

This rule should appear fifth in the list of default policies.

Example of a Policy to Require Encryption to
If you use Opportunistic Encryption with its default settings and you put it at the
bottom of the list of policies, it will cause those messages for which a verified key
cannot be found to be delivered in the clear. This ensures that your messages get sent,
but it also means that some may be sent in the clear.
If there are specific domains to which sending in the clear is not an option, you can
create a security policy that calls for encrypting and/or signing or the message is not
sent. When you create this policy, make sure it is higher in the list than Opportunistic
Encryption.
•

If: any

•

Conditions: Recipient Domain / is / example.com

•

Actions: Encrypt to / recipient’s verified key

•

Prefer message encoding: automatic

•

Key Not Found: Search keys.domain and / All Keyservers / temporarily cache
found keys

•

If no result: Block message

This security policy is similar to Require Encryption: [PGP] Confidential in that it
requires a message be encrypted or the message is not sent, but the criteria is not
whether the message is marked confidential but rather that the email domain of the
recipient is example.com. Using this policy ensures all messages to example.com are
encrypted with a verified key or they are not sent.

Example of a Policy to Sign and Send in the Clear to a Specific Domain
If you regularly send email to a domain for which you want to sign all messages but not
encrypt them, you should set up a policy for that domain.
•

If: any

•

Conditions: Recipient Domain / is / example.com

•

Actions: Sign

•

Prefer message encoding: automatic

Securing Email Messages
Working with the Security Policy List

Working with the Security Policy List
There are several important things you can do to the security policies in the list of
security policies, such as edit a policy, add a new policy (described in Creating a New
Security Policy (on page 86)), delete a policy, and change the order of policies in the list.

Editing a Security Policy
To edit an existing security policy
1

Open PGP Desktop and click the PGP Messaging item. The PGP Messaging screen
is displayed.

Click the name of the service with the security policy you want to edit. The
properties for the service you selected appear.

Select the security policy you want to edit, then click View Policy. The Message
Policy dialog box is displayed, displaying the settings for the specified policy.s
The default policies can be viewed, modified, and disabled, but not deleted.

Make the desired changes to the policy. For information about the fields on the
Message Policy dialog box, see Creating a New Security Policy (on page 86).

When you have made the desired changes, click OK to close the Message Policy
dialog box. The specified security policy is changed.

Editing a Mailing List Policy
To edit a default Mailing List policy
1

Open PGP Desktop and click the PGP Messaging item. The PGP Messaging screen
is displayed.

Click the name of the service with the security policy you want to edit. The
properties for the service you selected appear.

Securing Email Messages
Working with the Security Policy List

Select the mailing list policy you want to edit, then click View Policy. The Message
Policy dialog box is displayed, displaying the settings for the specified policy.

The default policies can be viewed, modified, and disabled, but not deleted.
4

Make the desired changes to the policy. In the first field, select:
•

If any. The policy applies when any condition is met.

•

If all. The policy only applies when all conditions are met.

•

If none. The policy only applies if none of the conditions are met.

In the first condition field, select:
•

Recipient. The policy applies only to messages to the specified recipient.

•

Recipient Domain. The policy applies only to email messages in the
specified recipient domain.

•

Sender. The policy applies only to messages with the specified sender
address.

•

Message. The policy applies only to messages which have the specified
signed and/or encrypted state.

•

Message Subject. The policy applies only to messages with the specified
message subject.

•

Note: Searching message headers in Lotus Notes and MAPI email systems is not
implemented, as messages in these systems do not include headers.

Securing Email Messages
Working with the Security Policy List

•

Message Body. The policy applies only to messages with the specified
message body.

•

Message Size. The policy applies only to messages of the specified size (in
bytes).

•

Message Priority. The policy applies only to messages with the specified
message priority.

•

Message Sensitivity. The policy applies only to messages with the specified
message sensitivity.

In the second condition field, select:
•

is. The condition is met when text in the first condition field matches the text
typed in the text box.

•

is not. The condition is met when text in the first condition field does not
match the text typed in the text box.

•

contains. The condition is met when text in the first condition field contains
the text typed in the text box.

•

does not contain. The condition is met when text in the first condition field
does not contain the text typed in the text box.

•

begins with. The condition is met when text in the first condition field begins
with the text typed in the text box.

•

ends with. The condition is met when text in the first condition field ends
with the text typed in the text box.

•

matches pattern. The condition is met when text in the first condition field
matches the pattern typed in the text box.

In the third condition field, in the text entry box, type the text for the matching
criteria.

In the Perform the following actions on the message section, in the first action
field, select:

•

Send In Clear. Specifies that the message should be sent in the clear; that is,
not signed nor encrypted.

•

Sign. Specifies that the message should be signed.

•

Encrypt to. Specifies that the message should be encrypted.

In the second action field, select:
•

recipient’s verified key. Ensures the message can be encrypted only to a
verified key of the intended recipient.

•

recipient’s unverified key. Allows the message to be encrypted to an
unverified key of the intended recipient.
recipient’s verified end-to-end key. Ensures the message can be encrypted
only to a verified end-to-end key of the intended recipient. An end-to-end key
is a key in sole possession of the individual recipient. In a PGP
Universal-managed environment, this is a Client Key Mode key which is
different from a Server Key Mode key, where the PGP Universal Server is in
possession of the key.
Whether the key is end-to-end or not is shown in the Group field on the Key
Properties dialog box on Windows systems or the Key Info dialog box on Mac
OS X systems. No means that the key is end-to-end (is not part of a group), and
Yes means that it is not end-to-end.)

Securing Email Messages
Working with the Security Policy List

•

recipient’s unverified end-to-end key. Allows the message to be encrypted
to an unverified end-to-end key of the intended recipient.

•

a list of keys. Specifies that the message can only be encrypted to keys on the
list.

In the prefer message encoding field, select:
•

automatic. Lets PGP Desktop choose the message encoding format. This is
almost always the best option unless you know exactly why you need to use
one of the other message encoding formats explicitly.

•

PGP Partitioned. Sets PGP Partitioned as the preferred message encoding
format. This format is the most backwards compatible with older PGP and
OpenPGP products.

•

S/MIME. Sets S/MIME as the preferred message encoding format. Choose
S/MIME if, for some reason, you need to force messages to be S/MIME even if
the user has a PGP key.

In the Recipient’s key is not available section, in the first Key Not Found field,
select:
•

Search keys.domain and. Specifies a search that includes both keys.domain
as well as another server you specify.

•

Search. Allows for searching for an appropriate key if one is not found on
the local keyring.

•

Clear-sign message. Specifies that the message should be sent in the clear,
but signed.

•

Send message unsecured. Specifies that the message be sent in the clear.

•

Block message. Specifies that the message must not be sent if an appropriate
key is not found.

In the second Key Not Found field, select:
•

All keyservers. Allows all keyservers, including the PGP Global Directory, to
be searched for an appropriate key.

•

PGP Global Directory or keyserver.pgp.com. Specifies that only the PGP
Global Directory is searched.

•

Edit Keyserver List. Lets you add keyservers to the list of currently
configured keyservers. This option is available only on Windows systems.

In the last Key Not Found field, specify:

Securing Email Messages
Working with the Security Policy List

•

ask to save found keys. Specifies that PGP Desktop should ask if you want to
save to your local keyring a particular found key.

•

save found keys. Specifies that found keys should automatically be saved to
your local keyring.

In the If no result field, select:
•

Clear-sign message. Allows messages for which an encryption key has not
been found to be signed and sent in the clear.

•

Send message unsecured. Do not encrypt message.

•

Block message. Prevents message for which an encryption key has not been
found from being sent.

When you have made the desired changes, click OK to close the Message Policy
dialog box. The specified security policy is changed.

Deleting a Security Policy
To delete an existing security policy
1

Click the name of the service with the security policy you want to delete. The
properties for the service you selected appear.

Deselect the check box next to the policy you want to delete.

Be sure the policy is still selected and click [ - ] at the bottom of the Security
Policies area. A confirmation dialog box is displayed.

Click Remove to delete the policy. The specified security policy is deleted from the
list.

Changing the Order of Policies in the List
To change the order of policies in the Security Policy list
1

In the PGP Messaging item, select the name of the service that has the security
policy whose order you want to change. The properties for the service you selected
appear.

From the Security Policies list, click on the name of the policy whose order in the
list you want to change. The specified policy highlights.

Click the Up arrow or Down arrow at the bottom of the Security Policies window
until the policy is in the desired location in the list.

100

Securing Email Messages
PGP Desktop and SSL

Note: Make sure Opportunistic Encryption is at the bottom of the list. Any
policy below it is not implemented.

PGP Desktop and SSL
When you use PGP Desktop, Symantec Corporation’s goal is for your data to be
automatically protected whenever possible. This includes protecting your data in
transit between your email client and your mail server.
Tip: SSL stands for Secure Sockets Layer, which is a cryptographic protocol that
secures communications between two devices; in this case, between your email client
or PGP Desktop and your mail server.
PGP Desktop protects your data to and from your mail server in different ways
depending on the circumstances. The following information applies only if you selected
Automatic (the default) for the SSL/TLS setting in the server settings dialog:
•

When the connection is not SSL protected. If the connection between your email
client and your mail server is not SSL protected, PGP Desktop will automatically
attempt to upgrade that connection to SSL (it will negotiate with your mail server
and upgrade the connection if the mail server supports it).
If the mail server does not support SSL, the message(s) PGP Desktop sends and
receives during the session will be over an unprotected connection. Whether or
not those messages will be encrypted or decrypted by PGP Desktop does not affect
the attempt by PGP Desktop to upgrade the connection. Messages encrypted by
PGP Desktop can be sent or received over a connection protected by SSL or not
protected by SSL.
Note: PGP Desktop always attempts to upgrade an unprotected connection to the
mail server to SSL protection because an SSL-protected connection not only
protects any non-PGP-encrypted messages on their way to the mail server or
coming from it, but it also protects your mail server authentication passphrase
when it is sent to the mail server.

•

When the connection is protected by SSL. If you have SSL protection turned on in
your email client for the connection to your mail server, you must turn it off if you
want PGP Desktop to encrypt or decrypt your messages; PGP Desktop cannot
process your messages if they are already SSL-encrypted.
Turning off SSL protection in your email client does not mean that your
non-PGP-encrypted messages are now unprotected going to or coming from your
mail server. As with any connection that is not SSL protected, PGP Desktop will
automatically attempt to upgrade the connection to SSL protection if the mail
server supports it (if you selected Automatic for the SSL/TLS setting in the server
settings dialog). If the mail server does not support SSL connections, the messages
PGP Desktop sends during the session will be over an unprotected connection.
The only time your messages will be sent in the clear to your mail server is if the
messages are not PGP encrypted and the connection to the mail server cannot be
upgraded to SSL protected, or you have selected the Do Not Attempt option in the
SSL/TLS setting.

Securing Email Messages
Key Modes

•

When you cannot have messages sent in the clear. Some security policies require
that only protected messages can be sent; in other words, unprotected messages
must never be sent. If necessary, you can configure PGP Desktop to support this
kind of security policy.
Select the applicable PGP Messaging service, access the Server Settings dialog box
(click the name of the server currently in the Server field of the Account
Properties for the service), and choose an option from the SSL/TLS list other than
Automatic.
When this option is enabled, PGP Desktop will only send messages to or receive
messages from your mail server if the connection between them is SSL protected.
If an SSL-protected connection cannot be established, PGP Desktop will not
interact with the server.
Note: This option should be enabled only if you are certain your mail server
supports SSL. It ensures that PGP Desktop will not fall back to sending or
receiving messages with the mail server over an unprotected connection if, for
example, a problem occurs while negotiating SSL protection for the connection.
If you enable this option and your mail server does not support SSL, PGP Desktop
will not send or receive any of your messages.

•

When you want SSL enabled in your email client. To use PGP Desktop with SSL
enabled in your email client, you must deselect the option to Warn if email client
attempts SSL/TLS for your incoming or outgoing mail server, or both. When you
disable this option for a connection to a mail server, PGP Desktop ignores
incoming and outgoing traffic over that connection when the connection is
protected by SSL.
PGP Desktop monitors the connections to and from this server, ignoring traffic
sent or received on SSL-protected connections. If, however, PGP Desktop detects a
non-SSL-protected connection, it handles the traffic like any other unprotected
connection and attempts to upgrade the connection to SSL (if in Automatic mode)
and apply applicable policies to messages.

Key Modes
If you are using PGP Desktop in a PGP Universal Server-managed environment, PGP
Desktop will have a key mode.
Note: The information in this section applies only to users of PGP Desktop in an
email domain protected by a PGP Universal Server.
Available key modes are:
•

Server Key Mode (SKM): Keys are generated on and managed by the PGP
Universal Server; they are only shared with the computer on which you are
running PGP Desktop as needed. Your private key is stored only on the PGP
Universal Server, which also handles all private key management. The PGP
Universal administrator has complete access to your private key and can thus
access all messages you encrypt. This key mode is not compatible with smart cards
(smart cards can be used on Windows systems only).
Starting with PGP Desktop version 10.0, SKM keys that previously could be used
only for messaging can be used for all other PGP Desktop encryption actions. This
includes encrypting disks and files, and decrypting MAPI email messages when
offline.

101

102

Securing Email Messages
Key Modes

If you are using an SKM key, you will never need to enter a passphrase for
authentication. SKM key passphrases are randomly generated by PGP Desktop and
are stored encrypted. When PGP Desktop requires a passphrase, PGP Desktop
retrieves the encrypted passphrase from your system without requiring
interaction from you.
•

Client Key Mode (CKM): Keys are generated on and managed by the computer on
which you are running PGP Desktop; private keys are not shared with the PGP
Universal Server. All cryptographic operations (encrypt, decrypt, sign, verify) are
also handled by the computer on which you are running PGP Desktop. On
Windows systems, this key mode is compatible with smart cards.

•

Guarded Key Mode (GKM): Very similar to CKM, except that an encrypted copy of
the private key is stored on the PGP Universal Server, which you can access if you
change computers. As the key is encrypted, the PGP Universal administrator
cannot access this private key, only you can. This key mode is compatible with
smart cards (on Windows systems only) as long as the key is not generated directly
on the smart card; that is, as long as the key is copied to the smart card.

•

Server Client Key Mode (SCKM): Also very similar to CKM, except that a copy of
the private encryption key is stored on the PGP Universal Server; private signing
keys never leave the computer on which you are running PGP Desktop. This key
mode ensures compliance with laws and corporate policies that require that the
private signing key not leave the control of the user, while making sure that the
private encryption key is stored in case of emergency. This key mode is compatible
with smart cards (on Windows systems only) as long as the key is not generated
directly on the smart card. SCKM requires a key with a separate signing subkey,
which can be created for a new key with PGP Desktop 9.5 or later or added to an
older PGP key using PGP Desktop 9.5 or later.

Depending on how your PGP administrator configured your copy of PGP Desktop, you
may or may not be able to choose your key mode. Also, you may or may not be able to
change your key mode.
Contact your PGP administrator if you have additional questions about your key mode.

Determining Key Mode
Remember that only PGP Desktop users in a PGP Universal-protected environment will
have a key mode; standalone PGP Desktop users do not have a key mode.
To determine your key mode
•

Open PGP Desktop and select the PGP Messaging service whose key mode you
want to determine. The account properties and security policies for the selected
service appear.
In the Universal Server field, the key mode for the selected service is shown in
parentheses after the name of the PGP Universal Server (for example,
keys.example.com (GKM)). This indicates that the key mode for the selected
service, in this example, is Guarded Key Mode and that the associated PGP
Universal Server is keys.example.com.

Changing Key Mode
Depending on how your PGP administrator configured your copy of PGP Desktop, you
may not be able to change your key mode.

Securing Email Messages
Viewing the PGP Log

To change your key mode
1

Open PGP Desktop and select the PGP Messaging service for the key mode you
want to change. The account properties and security policies for the selected
service appear.

Click Key Mode. The PGP Universal Key Mode screen is displayed, describing your
current key management mode.

Click Reset Key and then click Yes in the confirmation message displayed. The
PGP Key Setup Assistant is displayed.

Read the text, then click Next. The Key Management Selection screen is displayed.

Select the desired key mode. Depending on how your PGP Universal administrator
configured your copy of PGP Desktop, some key modes may not be available.

Click Next. The Key Source Selection screen is displayed.

Choose one of the following:
•

New Key. You will be prompted to create a new PGP key, which will be used
to protect your messaging.

•

PGP Desktop Key. You will be prompted to specify an existing PGP key to
use to protect your messaging.

•

Import Key. You will be prompted to import a PGP key, which will be used to
protect your messaging.

Make the desired selection, then click Next.

If you selected New Key, do the following:

•

Enter a passphrase for the key, then click Next.

•

When the key is generated, click Next.

•

Click Finish.

If you selected PGP Desktop Key, do the following:
•

Select the key from the local keyring that you want to use, then click Next.

•

Click Finish.

If you selected Import Key, do the following:
•

Browse to file that holds the PGP key you want to import (it must contain a
private key), then click Next.

•

Click Finish.

Viewing the PGP Log
Use the PGP Log to see what actions PGP Desktop is taking to secure your messages.
To view the PGP Log
1

Do one of the following:

103

104

Securing Email Messages
Using PGP Scripts with Entourage 2008

•

Click the PGP Desktop icon in the Menu Bar and select Show Log from the
menu. The PGP Log is displayed.

•

Open PGP Desktop and select Window > PGP Log. The PGP Log is displayed.

Do the following:
•

Click Clear to clear all of the entries in the PGP Log. You are prompted to
confirm you want to clear all entries in the log; click Yes.

•

Click Find to search the entries in the PGP Log. Enter the search terms and
click Next.

•

Click the arrow for Logging level to select the minimum information level of
log entries you want to view: Info or Verbose. Note that Verbose can result
in large log files.
To view Verbose logs, the PGP Log view window must remain open. When you
close the window, the level of logging reverts back to the default level, Info.
Note that Verbose can result in some large log files.

•

Click Save to save a copy of the entries in the log. Specify a file name,
location, and format (the default is a plain text file) for the log file, then click
Save.

Click the red circle in the upper left corner of the screen to close the PGP Log
window.

Using PGP Scripts with Entourage 2008
To use the PGP scripts in Entourage to encrypt email
1

Create your email message.

Click the Scripts icon listed in the Entourage toolbar, and select PGP.

Select the option to Encrypt or Encrypt & Sign, and select the key to sign to.

The email text is encrypted and a block of cipher text is displayed in its place.

You can now send your email securely.

To use the PGP scripts in Entourage to decrypt email
1

Open the encrypted email.

Click on the Scripts menu item and select PGP.

Select Decrypt & Verify and enter the passphrase when prompted. The email is
decrypted.

Securing Instant Messaging

This section provides information on how to use PGP Desktop to secure your instant
messaging (IM) sessions. For information about the PGP Options that affect IM
sessions, see Messaging Options (see "Messaging Preferences" on page 170).
Note: If you are using PGP Desktop in a PGP Universal Server-managed
environment, your PGP Universal Server administrator may have disabled certain
features. When a feature is disabled, the control item in the left side is not displayed
and the menu and other options for that feature are not available. The graphics
included in this guide depict the default installation with all features enabled. If your
PGP Universal Server administrator has disabled this functionality, this section does
not apply to you.

In This Chapter
About PGP Desktop Instant Messaging Compatibility ..........................................105
About the Keys Used for Encryption........................................................................106
Encrypting your IM Sessions.....................................................................................107

About PGP Desktop Instant Messaging Compatibility
PGP Desktop automatically encrypts AOL and iChat standard instant messaging
sessions, direct connects, and file transfers if the following conditions are met:
•

Both users in the IM session have PGP Desktop 9.0 or later installed and running
on the system on which they are using IM. To confirm that you are using PGP
Desktop 9.0 or later, click the PGP Tray icon and select About PGP from the
shortcut menu (from within the PGP Desktop window, select Help > About PGP).

•

Both users have the Encrypt instant messages setting enabled. To do this:
•

On Windows systems, select Tools > Options, click the Messaging tab, and
select the checkbox to Encrypt AOL Instant Messages (AIM).

•

On Mac OS X systems, select PGP > Preferences, click the Messaging icon,
and select the checkbox to Encrypt AOL Instant Messages (AIM).

Tip: On Windows systems, quickly verify that instant messaging encryption is
enabled by clicking the PGP Tray icon. There should be a check mark next to Use
PGP AIM Proxy in the shortcut menu.
•

Both users are using compatible IM clients. For information on the compatible IM
clients, see the following section.

•

The AIM address of the initiator of the IM session is on the Buddy List of the
recipient of the session (or the session will not be encrypted).

106

Securing Instant Messaging
About the Keys Used for Encryption

The secure IM feature is compatible with any IM client that supports AOL's OSCAR
protocol for instant messaging, such as AOL Instant Messenger, Trillian Pro, iChat and
Gaim.
The file transfer and direct connect sessions require recent versions of these clients in
order for PGP Desktop to encrypt them. In addition, Symantec Corporation
recommends that you set up the connection for both Direct IM/Direct Message and File
Transfer to use the AOL Proxy, rather than allowing your buddy to connect directly to
your computer.
Notes:
Audio and video connections are not encrypted by PGP Desktop.
PGP Desktop’s secure IM feature uses Perfect Forward Secrecy for enhanced
security. All keys used to secure your IM sessions are generated at the beginning of
the connection and then destroyed when you disconnect; completely new sets of keys
are used for every IM session. This adds an extra level of security to your IM
sessions.

Instant Messaging Client Compatibility
PGP Desktop is compatible with the following instant messaging clients when
encrypting AIM instant messages, file transfers, and direct connections:
•

iChat 4.0, 5.0 SL

Other instant messaging clients may work for basic instant messaging, but have not
been certified for use.

About the Keys Used for Encryption
A 1024-bit RSA key is generated each time you log onto your IM software, and is
destroyed when you log out. This key is used to exchange randomly generated seed data
with anyone with whom you communicate. The seed data is combined and hashed to
allow each participant in the communication to generate a set of symmetric keys used
for that particular communication (one for each direction). The symmetric keys are
used to encrypt all the messages with AES256.
Some of that data is also used to generate keyed-hash message authentication code, or
HMAC, for each message so that the message integrity can be checked.
Note: The keys used for secure IM communication are not user configurable.

Securing Instant Messaging
Encrypting your IM Sessions

Encrypting your IM Sessions
Once you have met the conditions described in About PGP Desktop’s Instant Messaging
Compatibility (see "About PGP Desktop Instant Messaging Compatibility" on page 105),
start your IM session as you normally would. Your IM sessions with any other PGP
Desktop user using a compatible IM client are automatically and transparently
protected.
There are multiple ways to verify that your IM session is being protected:
•

When you start an IM session, the PGP Notifier is displayed, informing you that a
secured IM session has begun.

•

When the IM session begins, the first message you see from the other user in the
session will have extra text below it that says: “Conversation encrypted by PGP
Desktop.”

•

If you open the PGP Log after you have started your IM session, you see entries
noting that the IM session is being proxied, that the session is being encrypted,
and so on, as in the following example:
2006-09-15 11:39:49 Proxying AIM connection from AliceIM using
Apple iChat.
Initiating PGP Desktop encrypted AIM session with JMedinaX using
your key with id 0x0910D29E.
Encrypted AIM session with JMedinaX established.

107

Viewing Email with PGP Viewer

This section provides information on how to use PGP Desktop to decrypt, verify, and
display encrypted messages using PGP Viewer.
Note: PGP Viewer only runs on systems with PGP Desktop installed. You cannot use
PGP Viewer standalone.

In This Chapter
Overview of PGP Viewer.............................................................................................109
Opening an Encrypted Email Message or File.........................................................110
Copying Email Messages to Your Inbox...................................................................111
Exporting Email Messages .........................................................................................111
PGP Viewer Preferences.............................................................................................112
Security Features in PGP Viewer ..............................................................................112

Overview of PGP Viewer
In normal usage, PGP Desktop sits between your email client (Mozilla Thunderbird, for
example) and your email server so that PGP Desktop can encrypt and sign outgoing
messages and decrypt and verify incoming messages. When PGP Desktop is doing this,
it is called “in the mail stream.”
Use PGP Viewer to decrypt, verify, and display messages outside the mail stream.
There are multiple ways you could have ended up with encrypted messages outside the
mail stream:
•

Encrypted messages saved securely. Many organizations store messages
encrypted for security purposes. Storing them puts them outside the mail stream,
but PGP Viewer can decrypt, verify, and display them while maintaining the
original encrypted message.

•

Encrypted text in a webmail message. Encrypted messages sent to a webmail
account cannot be decrypted by PGP Desktop. However, PGP Viewer can decrypt
those messages. Open the message.pgp file attachment using PGP Viewer or
copy/paste the encrypted text into PGP Viewer.

•

Encrypted text not decrypted by PGP Desktop. If a message was automatically
downloaded by your email client when PGP Desktop was not running or when your
passphrase was not cached, you could end up with encrypted message text that is
now outside the mail stream.

PGP Viewer decrypts, verifies, and displays multiple types of messaging content:
•

Modern PGP-encrypted content (PGP/MIME and PGP Partitioned)

•

Legacy PGP-encrypted content (PGP/MIME and PGP Partitioned)

110

Viewing Email with PGP Viewer
Opening an Encrypted Email Message or File

RFC-2822 compliant encrypted content PGP Viewer uses PGP Desktop keyrings for
operations that require keys. PGP Viewer honors applicable PGP Desktop preferences;
passphrase caching options, for example.
In a PGP Universal Server-managed environment, PGP Viewer searches for verification
keys per the applicable policy.
PGP Viewer displays signature information for messages it decrypts in the message
window, not in the message itself. This provides access to full signature information
and prevents spoofing of inline signature annotations.

Supported Email Clients
Use PGP Viewer to copy the text of a decrypted/verified message to the following email
clients:
•

Windows Mail (Windows)

•

Microsoft Outlook (Windows)

•

Thunderbird (Windows and Mac OS X)

•

Outlook Express (Windows)

•

Lotus Notes (Windows)

•

Mail.app (Mac OS X)

Due to the design of Lotus Notes architecture, an encrypted message cannot be dragged
from Lotus Notes email client and dropped into PGP Viewer to be decrypted.

Opening an Encrypted Email Message or File
Use PGP Viewer to open (decrypt, verify, and display) encrypted message files of the
following types:
•

.pgp: Created by a PGP application.

•

.eml: Created by Outlook Express or Thunderbird.

•

.emlx: Created by Apple's Mail.app program on Mac OS X systems.

•

.msg: Created by Microsoft Outlook.

When PGP Viewer opens an encrypted message, it does not overwrite the encrypted
text. The original message remains intact.
To decrypt, verify, and display an encrypted message from a file
1

Open PGP Desktop and select the PGP Viewer tab.

Click Open File in PGP Viewer or select Viewer > Open File in PGP Viewer.

In the Open Message File dialog box, navigate to the file you want to open, select
it, then click Open. PGP Viewer decrypts, verifies, and displays the message in a
separate window.

Viewing Email with PGP Viewer
Copying Email Messages to Your Inbox

Note: You can drag and drop the file you want to decrypt onto the portion of the
PGP Viewer screen that displays: Drag Email or Files Here. PGP Viewer opens
the file, decrypts and verifies it, and displays the message.
4

To open another message, click Open Message in the toolbar, navigate to the
desired file, select it, then click Open. PGP Viewer decrypts, verifies, and displays
the message.

Click Smaller to make text smaller or Bigger to make text larger.

Click Rich Text to display the message or file in RTF (rich text format) or Plain
Text for plaintext.

Click Print to print the message or file.

Copying Email Messages to Your Inbox
Use PGP Viewer to copy plaintext versions of messages that have been decrypted to the
inbox of your email client.
To copy a message to the inbox of your email client
1

With the desired message in the PGP Viewer window, click Copy to Inbox .
The Copy to Inbox confirmation dialog box is displayed. If you do not want to view
this confirmation in the future, select the checkbox to Don't display this again.
The Copy to Inbox confirmation dialog box displays the name of the email client
to which the message will be copied. To change this setting, see PGP Viewer
Preferences.

Click OK to continue.
If you are copying a message to the Mozilla Thunderbird email client for the first
time, a dialog box is displayed advising that you must install an add-on.

Click Yes to install the add-on and follow the on-screen instructions or click No.
You must be using Thunderbird 2.0 or greater to install the add-on.
PGP Viewer opens your email client and copies a plaintext version of the message
to the inbox.

Exporting Email Messages
Use PGP Viewer to export a decrypted message to a file.
To export a message from PGP Viewer to a file
1

With the message displayed in the PGP Viewer window, click Export.

In the Export Message dialog box, specify the desired filename, location, and
format for the file, then click Export.
PGP Viewer saves the file to the specified location.

111

112

Viewing Email with PGP Viewer
PGP Viewer Preferences

PGP Viewer Preferences
PGP Viewer includes preferences that provide control of certain functionality.
To access PGP Viewer preferences
1

Open PGP Viewer or use PGP Viewer to decrypt, verify, and display a message.

Pull down the PGP Viewer menu and select Preferences.
The Preferences dialog box appears.

Select the General tab and specify the following preferences:
•

Ask for confirmation when using Copy to Inbox: Controls whether or not a
confirmation prompt is displayed when you copy text from PGP Viewer to
the inbox of your email client. The default is enabled.

•

Automatically load remote images in HTML messages: Controls whether
external resources like images, CSS style sheets, or iframe content, for
example, are automatically loaded by PGP Viewer. The default is disabled, as
this may be a security risk.

•

Email Client: Lets you specify the email client to which PGP Viewer will copy
content. The default is the system default email client (PGP Viewer
determines your default system email client and uses that as its default). You
can select Mail.app or Thunderbird.

Select the Fonts and Colors tab specify the following preferences:
•

Font: Controls the font PGP Viewer uses to display text. Click Select, then
specify the desired Collection, Family, Typeface, and Size.

•

Text Color: Controls the color of text that PGP Viewer displays. Click the
color block and select the desired color.

•

Background Color: Controls the background color of text that PGP Viewer
displays. Click the color block and select the desired color.

Security Features in PGP Viewer
PGP Viewer proactively protects your security:
•

The Web browser embedded in PGP Viewer, which displays messaging content,
has JavaScript, Java Applets, and plugins disabled. This prevents an attacker from
delivering a malicious payload that PGP Viewer might otherwise load.

•

External resources — images, CSS style sheets, iframe content (an inline frame
that contains another document), and so on — are loaded automatically based on
the Automatically load remote images preference. For security purposes, this
preference is disabled by default. When this preference is disabled, PGP Viewer
does not generate any network traffic to external sites.

Viewing Email with PGP Viewer
Security Features in PGP Viewer

113

Protecting Disks with PGP Whole Disk
Encryption
PGP Whole Disk Encryption (PGP WDE) locks down the entire contents of a laptop,
desktop, external drive, or USB flash drive, including boot sectors, system files, and
swap files. Encryption runs as a background process that is transparent to you,
automatically protecting valuable data without requiring you to take additional steps.
Note: If you are using PGP Desktop in a PGP Universal Server-managed
environment, your PGP Universal Server administrator may have disabled certain
features. When a feature is disabled, the control item in the left side is not displayed
and the menu and other options for that feature are not available. The graphics
included in this guide depict the default installation with all features enabled. If your
PGP Universal Server administrator has disabled this functionality, this section does
not apply to you.
If you are using PGP Desktop in a PGP Universal Server-managed environment, your
PGP administrator may have specified, by policy, that all boot drives must be
encrypted. If this is the case, PGP Desktop periodically verifies that drives are
encrypted and will enforce policy by automatically encrypting unencrypted boot
drives.
If you are using PGP Desktop in a PGP Universal Server-managed environment, your
PGP administrator may have specified, by policy, that all system disks must be
encrypted. If this is the case, PGP Desktop periodically verifies that disks are
encrypted and will enforce policy by automatically encrypting unencrypted system
disks.

In This Chapter
About PGP Whole Disk Encryption ..........................................................................116
Licensing PGP Whole Disk Encryption ....................................................................117
Prepare Your Disk for Encryption ............................................................................118
Determine the Authentication Method for the Disk..............................................121
Encrypting a Disk ........................................................................................................121
Using a PGP-WDE Encrypted Disk ...........................................................................125
Maintaining the Security of Your Disk ....................................................................126
Using PGP WDE in a PGP Universal Server-Managed Environment..................130
Recovering Data From an Encrypted Drive.............................................................131
Decrypting an Encrypted Disk ..................................................................................133
Moving Removable Disks to Other Systems............................................................133
Accessing Data on Encrypted Removable Disks.....................................................134
Special Security Precautions Taken by PGP Desktop............................................134
Technical Details About Encrypting Boot Disks.....................................................135

116

Protecting Disks with PGP Whole Disk Encryption
About PGP Whole Disk Encryption

About PGP Whole Disk Encryption
Use the PGP WDE feature to fully encrypt the boot disk (Intel-based Macintoshes only)
and external disks on Mac OS X systems. You can also use it to fully encrypt
Windows-formatted external disks.
Important: PGP Desktop 9.9 and later use a different partitioning method than did
versions of PGP Desktop prior to Version 9.9. If you used the PGP WDE feature of
versions of PGP Desktop prior to Version 9.9, you must decrypt those disks before
installing Version 10.2 or you will no longer be able to access the data on them.
When you encrypt an entire disk using the PGP WDE feature, every sector is encrypted
using a symmetric key. This includes all files including operating system files,
application files, data files, swap files, free space, and temp files.
On subsequent reboots, PGP WDE prompts you for the correct passphrase. Then the
encrypted data is decrypted as you access it. Before any data is written to the disk, PGP
WDE encrypts it. As long as you are authenticated to your PGP WDE-encrypted disk
(after you have entered the correct passphrase at the PGP BootGuard screen), the files
are available. When you shut down your system, the disk is protected against use by
others.
If your system supports the Intel® Advanced Encryption Standard (AES) Instructions
(AES-NI), your system is encrypted and decrypted using the hardware associated with
this encryption algorithm. AES-NI provides enhanced performance during encryption
and decryption processes.
Before encrypting your disk with PGP WDE, it is important to understand the process of
creating and using a PGP WDE-encrypted disk:
1

Make sure that your PGP Desktop license supports its use, as described in
Licensing PGP Whole Disk Encryption (on page 117).

Perform the tasks to Prepare Your Disk for Encryption (on page 118).

Choose how you want to authenticate yourself to encrypt the disk in Determine the
Authentication Method for the Disk (on page 121).

Start the encryption process in Encrypting a Disk (on page 121).

Learn how to use an encrypted disk in Using a PGP WDE-Encrypted Disk (see
"Using a PGP-WDE Encrypted Disk" on page 125).

Learn how to maintain your encrypted disk in Maintaining the Security of Your
Disk (on page 126).

Learn how to decrypt the disk, if needed, in Decrypting a PGP WDE-Encrypted Disk
(see "Decrypting an Encrypted Disk" on page 133).

Understand the features that help avoid security problems in Special Security
Precautions Taken by PGP Desktop (on page 134).

If you are a PGP Universal Server Administrator, or are using PGP WDE in a PGP
Universal Server-managed environment, see Using PGP WDE in a PGP Universal
Server-Managed Environment (on page 130) for additional information.

Protecting Disks with PGP Whole Disk Encryption
Licensing PGP Whole Disk Encryption

Warning: Once you unlock a disk, its files are available to you—as well as anyone else
who can physically use your system. Your files are decrypted until you encrypt them
again by shutting down your computer. Use a PGP Virtual Disk volume for files that
need to be secured even while your computer is in use. For more information, see
Using PGP Virtual Disks (on page 137).

Encrypting Boot Disks
Starting with PGP Desktop for Mac OS X version 10.2, you can fully encrypt the boot
disk on an Intel-based Macintosh. You can, of course, continue to encrypt removable
disks, and USB flash disks as you could with versions of PGP Desktop prior to Version
10.2.
Important: Apple's Boot Camp product works only when PGP Desktop and Apple Boot
Camp are installed in a specific order. For more information, see Using PGP Desktop
with Apple Boot Camp (on page 16)
The PGP WDE feature supports both 32- and 64-bit Intel-based Mac OS X systems.
Note: The Mac OS X Safe Boot feature does not work on a boot disk that has been
whole disk encrypted; Safe Boot disables kernel extensions required by PGP WDE. If
you hold down the Shift key after authenticating at the PGP BootGuard screen, the
system will not boot; however, it does restart after a few minutes.

How does PGP WDE Differ from PGP Virtual Disk?
The PGP Virtual Disk feature differs from PGP WDE in that PGP Virtual Disks perform
like additional volumes on your system that can be locked, even while you are using
your computer. These volumes are like a vault where you can store files needing
protection. There is no actual physical disk, only the virtual one that the PGP Virtual
Disk feature creates and manages.
PGP WDE protects your entire physical hard disk.
Both products work independently of each other, so you can use them at the same time.
For more information, see Using PGP Virtual Disks (on page 137).

Licensing PGP Whole Disk Encryption
To use the PGP Whole Disk Encryption feature, your copy of PGP Desktop must have a
license that supports it.
To verify your license supports PGP Whole Disk Encryption
1

Open PGP Desktop.

From the PGP menu, select License. The License Information dialog box is
displayed.

Click Details. The details of your license are displayed. In the Enabled Features
section, verify that PGP Whole Disk Encryption is listed.

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Protecting Disks with PGP Whole Disk Encryption
Prepare Your Disk for Encryption

If your license does not support PGP WDE, you can find more information about
licensing PGP Desktop using one of the following methods:
•

If you are using PGP Desktop in a PGP Universal Server-managed environment,
contact your PGP administrator for more information about support for the PGP
WDE feature in your license. For more information, see Using PGP Desktop with
PGP Universal Server (on page 185).

•

If you are using PGP Desktop outside of a PGP Universal Server-managed
environment, go to the Symantec website (http://www.symantec.com) for more
information about adding the PGP WDE feature to your license.

License Expiration
PGP WDE used under a subscription license basis provides a 90-day post-license
expiration decryption feature for boot disks only. Ninety days after the subscription
license expires, the PGP WDE feature decrypts your data (after notifying you) so you
can retrieve your files.

Prepare Your Disk for Encryption
Before you encrypt your disk, there are a few tasks you must perform to ensure
successful initial encryption of the disk.
•

Determine whether your target disk is supported. See Supported Disk Types (on
page 119).

•

Make sure you use supported characters in your passphrase. See Supported
Characters (on page 122).

•

Ensure the health of the disk before you encrypt it. If PGP Desktop encounters
disk errors during encryption, it will pause encryption so you can repair the disk
errors. However, it is more efficient to repair errors before you initiate encryption.
See Ensure Disk Health Before Encryption (on page 120).

•

Back up the disk before you encrypt it. Before you encrypt your disk, be sure to
back it up so that you will not lose any data if your laptop or computer is lost,
stolen, or you are unable to decrypt the disk. Also be sure to make regular backups
of your disk.

•

Consider the time it will take to encrypt the disk and prepare accordingly. See
Calculate the Encryption Duration (on page 120).

•

Run a pilot test to ensure software compatibility. As a good security practice,
Symantec Corporation recommends testing PGP Desktop on a small group of
computers to ensure that PGP Desktop is not in conflict with any software on the
computer before rolling it out to a large number of computers. This is particularly
useful in environments that use a standardized Corporate Operating Environment
(COE) image. Certain other disk protection software is incompatible with PGP
Desktop and can cause serious disk problems, up to and including loss of data. See
Run a Pilot Test to Ensure Software Compatibility (on page 121) for known
interoperability issues, and review the PGP Desktop Release Notes for the latest
updates to this list.

Protecting Disks with PGP Whole Disk Encryption
Prepare Your Disk for Encryption

Supported Disk Types
The PGP WDE feature protects the contents of the following types of disks:
•

Desktop or laptop disks, including solid-state drives.
Note: Do not use PGP WDE to encrypt server hardware. PGP WDE is not
supported on Mac OS X server hardware.

•

External disks, excluding music devices and digital cameras.

•

USB flash disks, sometimes called thumb drives.

There is no minimum or maximum size for a PGP WDE-encrypted disk. If the disk is
supported by the operating system (or your hardware BIOS for the boot disk or
partition), it should work with PGP Desktop.
If you want to partition a drive that has been encrypted with PGP WDE, you must first
decrypt the drive. After you have decrypted the drive, you may partition it.
PGP WDE supports normal Sleep mode. Safe Sleep, or Hibernation, is not supported and
is automatically disabled.

Unsupported Disk Types
The following disk types are not supported:
•

Disks formatted using the APM partition scheme.

•

Any type of server hardware, including RAID disk drives.

•

Diskettes and CD-RW/DVD-RWs.

Supported Keyboards
The PGP BootGuard log-in screen supports the following keyboard layouts:
•

English (US-International)

•

Japanese (Japan)

•

German (Germany)

•

German (Switzerland)

•

French (France)

•

French (Switzerland)

•

Spanish (Latin America)

•

Spanish (Spain; ISO)

Different keyboard layouts can have different mappings between characters,
potentially causing problems when you enter your passphrase to authenticate. Be sure
to specify the supported keyboard layout (in System Preferences > Personal >
International), and then make sure to use that same layout each time you authenticate.

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Protecting Disks with PGP Whole Disk Encryption
Prepare Your Disk for Encryption

Note: Not all keyboards are named the same in different languages. If selecting
"English (US-International)" does not work at PGP BootGuard, select "USA."

Ensure Disk Health Before Encryption
Symantec Corporation deliberately takes a conservative stance when encrypting drives,
to prevent loss of data. It is not uncommon to encounter Cyclic Redundancy Check
(CRC) errors while encrypting a hard disk. If PGP WDE encounters a hard drive with bad
sectors, PGP WDE will, by default, pause the encryption process. This pause allows you
to remedy the problem before continuing with the encryption process, thus avoiding
potential disk corruption and lost data.
To avoid disruption during encryption, Symantec Corporation recommends that you
start with a healthy disk by correcting any disk errors prior to encrypting.
Note: If you are using PGP Desktop in a managed environment, the bad sectors
encountered during encryption are logged to the management server and the
encryption process continues.

Best Practices Recommendation
As a best practice, before you attempt to use PGP Desktop to encrypt your disk, use a
third-party scan disk utility that has the ability to perform a low-level integrity check
and repair any inconsistencies with the drive that could lead to CRC errors. These
software applications can correct errors that would otherwise disrupt encryption.
If you are using Apple Boot Camp, Symantec Corporation recommends that you
perform all encryption and decryption operations from the Mac OS X partition. Be sure
that you have installed PGP Desktop on both the Mac OS X and Windows partitions
first, before booting into the Mac OS X partition to encrypt or decrypt.

Calculate the Encryption Duration
Encryption is a time-consuming and CPU-intensive process. The larger the disk being
encrypted, the longer the encryption process takes. You should consider this as you
schedule initial encryption of the disk.
Factors that may affect encryption speed include:
•

the size of the disk

•

the processor speed and number of processors

•

the number of system processes running on the computer

•

the number of other applications running on the system

•

the amount of processor time those other applications require

With an average system, an 80 GB boot disk takes approximately three hours to encrypt
using PGP Desktop (when no other applications are running). A very fast system, on the
other hand, can easily encrypt such a disk in less than an hour.
You can still use your system during encryption. Your system is somewhat slower than
usual during the encryption process, although it is fully usable.

Protecting Disks with PGP Whole Disk Encryption
Determine the Authentication Method for the Disk

PGP Desktop automatically slows the encryption process if you are using the system.
The encryption process is faster if you avoid using your computer during the initial
encryption. The system returns to normal operation when the encryption process is
complete.
If you decide to run other applications during the encryption process, those
applications will probably run slightly slower than normal until the encryption process
is over.

Run a Pilot Test to Ensure Software Compatibility
As a good security practice, Symantec Corporation recommends testing PGP Desktop
on a small group of computers to ensure that PGP Desktop is not in conflict with any
software on the computer before rolling it out to a large number of computers.

Determine the Authentication Method for the Disk
When you encrypt a disk using PGP WDE, you choose a method that determines how
you will authenticate yourself to decrypt the disk.
You have the following options:
•

Passphrase. With passphrase authentication, you specify a passphrase when
encrypting a disk. When attempting to access the encrypted disk, you must enter
the passphrase.

•

Public key. With public-key authentication, you specify a public key when
encrypting a disk. Only the holder of the corresponding private key can access the
contents of the disk. To do that, they must provide the passphrase of their private
key. Public key authentication is available only for removable disks you use with
your system. Fixed disks, including boot disks or disks in USB enclosures, must be
encrypted using a passphrase user.

During initial encryption of a boot disk, you can only select passphrase authentication
as the authentication method. After initial encryption, you can add additional
passphrase users to the disk.
During initial encryption of a non-boot disk (such as an external disk), you can select
between passphrase or public-key authentication.

Encrypting a Disk
Once you have prepared the disk, you can encrypt it. Note the following before you
begin:
•

Your system is somewhat slower than usual during the encryption process,
although it is fully usable. It returns to normal operation when the encryption
process is complete.
PGP Desktop automatically slows the encryption process if you are using the
system. The encryption process is faster if you avoid using your computer during
the initial encryption.

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Protecting Disks with PGP Whole Disk Encryption
Encrypting a Disk

•

You can minimize or close PGP Desktop during encryption. This does not affect
the process, but it does improve the speed of the encryption process.

•

To stop the encryption process for a short time, click Stop, then click Pause on the
dialog box. Click Resume to restart. You may need to authenticate after you click
Resume.

•

To shut down the system before the encryption process is over, perform a normal
shutdown. You do not need to pause the process. When you restart, the encryption
process automatically resumes where it left off.

You can only encrypt, decrypt, or re-encrypt one disk at a time. Once you begin an
operation on a disk, you cannot start encrypting another one until the process is
complete on the first. You cannot circumvent this by pausing the first operation.

Supported Characters
PGP Desktop supports alphanumeric characters, punctuation characters, and standard
meta-characters when creating passphrases or passwords. Tab and control characters
are not supported. As you choose a passphrase or password, please note the following.
•

The following characters are supported:
abcdefghijklmnopqrstuvwxyz
ABCDEFGHIJKLMNOPQRSTUVWXYZ
0123456789
`~!@#$%^&*()_+={}\|:;[]'"<>,.?/
Most extended ASCII characters (such as ç é è ê ë î ï ô û ù ü ÿ) or symbols
(such as ¢ ® œ), are supported.

Encrypting the Disk
Before you encrypt your disk, be sure to back it up so that you will not lose any data if
your laptop or computer is lost, stolen, or you are unable to decrypt the disk.
Caution: While your disk is encrypting, do not accept any operating system updates if
they are offered. If the update occurs automatically, do not restart your computer
until the encryption process has completed.
To protect a disk using the PGP Whole Disk Encryption feature
1

Open PGP Desktop and click on the PGP Disk item. The PGP Disk screen is
displayed.

Protecting Disks with PGP Whole Disk Encryption
Encrypting a Disk

Click Encrypt Whole Disk. The Encrypt Whole Disk screen is displayed, showing a
listing of disks on your system that can be protected.

From the Select a disk list, click on the disk you want to protect.

In the Secure with section, specify how you want to access your protected disk:
Public Key User or Passphrase User.
Note: If you are encrypting a boot disk, you can only use passphrase
authentication, so PGP Desktop selects Passphrase User for you and jumps
directly to the Add PGP Whole Disk User screen.
•

If you want to protect your disk with a public key, select Public Key, then
click Continue. The Add PGP Whole Disk User screen is displayed. This
option is not available if you have already encrypted your disk.
Select a key from the list, then click Continue. The Enter PGP Passphrase
dialog box is displayed.
Type the passphrase for the key you selected, then click OK. The PGP Whole
Disk Encryption Summary screen displays, showing you a summary of how
your disk is going to be encrypted, what key is used, and so on.

•

If you want to protect your disk with a passphrase, select Passphrase, then
click Continue. The Add PGP Whole Disk User screen is displayed.
Type a Name (or accept the default name), then type the desired passphrase in
the Enter your passphrase field, and then type it again in the Confirm your
passphrase field. To see your passphrase as you type, select Show Keystrokes.
The Passphrase Quality bar provides a basic guideline for the strength of the
passphrase you are creating by comparing the amount of entropy in the
passphrase you type against a true 128-bit random string (the same amount of
entropy in an AES128 key). For more information, see The Passphrase Quality
Bar (on page 180).

Click Continue. The PGP Whole Disk Encryption Summary screen is displayed,
showing you a summary of how your disk is going to be encrypted, what key is
used, and so on.

Review the information displayed. If you want to enable Power Failure Safety,
select the check box.

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Protecting Disks with PGP Whole Disk Encryption
Encrypting a Disk

While you can pause the initial encryption process at any time by properly
shutting down or restarting your computer, it is exceptionally important to avoid
unexpected shutdowns (power failures, power cord gets pulled out, and so on). If
this is a possibility for you—or if you do not have an uninterruptible power supply
for your computer—consider choosing the Power Failure Safety option. When
Power Failure Safety is selected, encrypting is journaled; if the power fails, the
encryption process can safely and accurately resume where it was interrupted.
However, this option can cause initial encryption to take several times longer to
complete.
This is also useful when encrypting USB devices. Interrupting encryption by
removing a USB device during encryption can corrupt the device and require that
it be reformatted. Encrypting with Power Failure Safety mode permits you to
remove the USB device during encryption and resume encryption once it is
reinserted.
7

Click Encrypt. The encryption process begins and the Encryption Progress screen
is displayed.

Click Close. The PGP Desktop screen is displayed; the encryption process
continues in the background. A progress bar shows how the encryption process is
progressing.
Note: The encryption process continues even if you close the Encryption
Progress screen. However, you can not see the progress bar until you close this
screen.

During the encryption process, you can do the following:
•

To temporarily stop the encryption process, click Stop. The Encryption is not
complete dialog box is displayed.

•

Pause the encryption process, Decrypt the portion of the disk that is already
encrypted, or Cancel to close the dialog box and continue with the
encryption process.

Note: If the encryption process stops and PGP Desktop indicates a disk
read/write error, it means that PGP Desktop has encountered bad sectors on your
disk during the encryption process. Immediately reverse the encryption process
by decrypting the portion of the disk that has been encrypted. Then use your disk
verification tools to find and resolve the problem.
When the encryption process completes, the disk properties for the encrypted disk
is displayed and include the description, type of disk, size, encrypted status, and
the user access information.

Encountering Disk Errors During Encryption
Many hard disks have bad sectors. If PGP WDE encounters bad disk sectors during
encryption, encryption pauses and you are warned that of the disk errors. (Note that
these errors are unrelated to encryption; they are an indication that your hard disk
needs maintenance.) The bad sectors encountered during encryption are logged to the
management server and the encryption process continues.
You can do one of the following:
•

Force encryption to continue by clicking Yes. Disk errors are frequently
encountered and often harmless. Clicking Yes will continue the encryption
process and PGP WDE ignores further errors.

Protecting Disks with PGP Whole Disk Encryption
Using a PGP-WDE Encrypted Disk

•

Stop encryption by clicking No, completely decrypt the disk, and then repair the
disk errors using a disk utility tool before making another attempt to encrypt the
disk. If you know that your disk has many bad sectors, you should immediately
perform the maintenance that your hard disk needs before encrypting the disk.

Using a PGP-WDE Encrypted Disk
Your computer boots up in a different way once you use PGP Whole Disk Encryption to
protect the boot disk—or a secondary fixed disk—on your system. On power-up, the first
thing you see is the PGP BootGuard log-in screen asking for your passphrase. When you
successfully enter a valid passphrase or password, PGP WDE then decrypts the disk.
When you use a PGP WDE-encrypted disk, it is decrypted and opened automatically as
needed. With most modern computers, after the disk is completely encrypted, there is
no noticeable slowdown of your activities.
Once you unlock a disk, its files are available to you—as well as anyone else who can
physically use your system. Your files are decrypted until you encrypt them again by
shutting down your computer.
Warning: Because your files remain decrypted until you encrypt them again, you may
want to use a PGP Virtual Disk volume for files that need to be secured even while
your computer is in use. See Using PGP Virtual Disks (on page 137).
When you shut down a system with an encrypted boot disk, or if you remove an
encrypted removable disk from the system, all files on the disk remain encrypted and
fully protected—data is never written to the disk in an unencrypted form. Proper
authentication (passphrase or private key) is required to make the files accessible again.

Authenticating at the PGP BootGuard Screen
The PGP BootGuard log-in screen prompts you for the proper passphrase for a
protected disk or partition The PGP BootGuard log-in screen prompts you for the
proper passphrase for a protected disk for one of two reasons:
•

If your boot disk is protected using PGP Whole Disk Encryption, you must
authenticate correctly for your system to start up. This is required because the
operating system files that control system startup are encrypted, and must be
decrypted before they can be used to start up the system.

•

If a secondary fixed disk is protected using PGP Whole Disk Encryption, you can
authenticate at startup so that you do not have to authenticate later when you
need to use files on the secondary disk. Because the files on the secondary
(non-boot) disk are not required for startup, you are not required to authenticate
at startup. If you do not authenticate at startup, you are asked to authenticate
later, when you try to use the files on the secondary disk or partition.
Note: The PGP BootGuard log-in screen accepts the authentication information from
any user configured for an encrypted disk. For example, if you have two users
configured for a boot disk and two different users configured for a secondary fixed
disk on the same system, any of the four configured users can use their passphrase to
authenticate on the PGP BootGuard log-in screen at startup, even the two users
configured on the secondary disk.

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Protecting Disks with PGP Whole Disk Encryption
Using a PGP-WDE Encrypted Disk

On the PGP BootGuard log-in screen you can authenticate an encrypted boot or
secondary disk on the system.
To authenticate using the PGP BootGuard log-in screen
1

Start or restart the system that has a disk protected by PGP Whole Disk
Encryption. On startup, the PGP BootGuard log-in screen is displayed.

Type a valid passphrase and press Enter.
Note: Some characters cannot be entered at the PGP BootGuard screen. See
Supported Characters (on page 122).
To see the characters you type, press Tab before you begin typing.
If you make a typing error, or think you might have made a typing error, press Esc
to clear all characters and start again.

If you typed a valid passphrase, the PGP BootGuard log-in screen goes away and
the system boots normally.
If you typed an invalid passphrase, an error message is displayed. Try typing the
passphrase again.

Protecting Disks with PGP Whole Disk Encryption
Maintaining the Security of Your Disk

Authenticating With a User Name
If you are using PGP Desktop in a PGP Universal Server-managed environment, your
administrator may require authenticating at PGP BootGuard with your user name. The
PGP BootGuard screen displays fields for you to enter your user name and passphrase.
Depending on the settings specified by your administrator, the information in the user
name field may be filled in automatically based on the last information entered. The
passphrase you enter is the one you created when you added a user and encrypted your
disk. When you have entered the correct information, the system continues to boot into
the operating system.

Maintaining the Security of Your Disk
The following sections describe how to work with your disk once you have encrypted it
with PGP Desktop.

Viewing Key Information on an Encrypted Disk
To view key information of a public key user on an encrypted disk
1

Select the encrypted disk with the public key user whose key information you
want to view.

In the User Access list, either Ctrl+click the user’s name or right-click it if you are
have a two-button mouse.

In the shortcut menu, select Show Key Info. The Key Info screen for the specified
key is displayed.

Modifying the System Partition
Do not make any changes to the system partition on a boot disk that has been encrypted
by PGP Desktop; it will fail to boot properly on the next startup. If you must make
changes to the partitioning of an encrypted disk, decrypt the disk first and then make
the partition changes.

Adding Other Users to an Encrypted Disk
The user who creates an encrypted disk can make it available to others. These
additional users can access the encrypted disk using their own unique passphrase or
private key. You can have up to 120 users per encrypted disk
Caution: Having multiple users who can access a disk protected by PGP Whole Disk
Encryption serves as a backup in case one person forgets their password. Users
configured for an encrypted disk can authenticate at the PGP BootGuard log-in
screen to unlock any protected disk on that system.

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Protecting Disks with PGP Whole Disk Encryption
Maintaining the Security of Your Disk

To add additional users to a disk protected by PGP Whole Disk Encryption
1

Select the encrypted disk to which you want to add another user.

Click the plus sign icon (+) below the User Access list.

Select Add Public Key User or Add Passphrase User, from the list displayed.
•

If you select Add Public Key User, you are prompted to select the public key
of the user(s) you want to add. Drag the users you want to add from the Key
Source column into the Keys to Add column, then click OK.

•

If you select Add Passphrase User, you are prompted for a user name and a
passphrase for the user you want to add. In the Username field, enter a user
name for the user you are adding.
In the Enter a passphrase for this user field, enter a passphrase. In the
Confirm user’s passphrase field, enter the same passphrase again. To see your
passphrase as you type, select Show Keystrokes.
Click OK.

You are prompted for the passphrase of the encrypted disk.
4

Enter the passphrase of the encrypted disk, then click OK. The specified public key
user(s) or passphrase user is added.
Note: Public-key encryption is the most secure protection method when adding other
users to disks encrypted with PGP Whole Disk Encryption because: (1) There is no
need to reveal passphrases to new users, so the risk of passphrases being intercepted
or overheard is minimal. (2) Other users do not need to memorize another
passphrase. (3) It is easier to manage lists of users if each uses their own private key
to access the disk.

Deleting Users From an Encrypted Disk
At some point you may want to remove the ability of a user to access an encrypted disk.
To remove a user from an encrypted disk
1

Select the encrypted disk from which you want to remove a user.

From the User Access list, select the name of the user you want to remove.

Click the minus sign icon (–) below the User Access list. You are prompted for the
passphrase of the encrypted disk.

Enter the passphrase of the encrypted disk, then click OK. The alternate user is
removed.
Note: You cannot remove all users from an encrypted disk; when only one user is
listed in the User Access list, you cannot remove that user.

Protecting Disks with PGP Whole Disk Encryption
Maintaining the Security of Your Disk

Changing User Passphrases
To change the passphrase of a passphrase user on an encrypted disk
1

Select the encrypted disk with the user whose passphrase you want to change.

In the User Access list, either Ctrl+click the user’s name or right-click it if you
have a two-button mouse.

From the shortcut menu, select Change User Passphrase. You are prompted for
the passphrase of the encrypted disk.

Enter the passphrase of the encrypted disk, then click OK. The Confirm PGP
Passphrase screen is displayed.

Type a new passphrase in the Enter your new passphrase box, move to the
Confirmation field and type the new passphrase again, then click OK.

Click OK on the Passphrase Changed box. The passphrase is changed.

Re-Encrypting an Encrypted Disk
Consider re-encrypting a protected disk that you suspect of having a password or
passphrase that has been compromised.
To re-encrypt a disk, the PGP Desktop feature uses the same encryption algorithm (AES
256)—but a different underlying encryption key—to encrypt the disk again. The result is
as if you decrypted the disk and encrypted it again, but much faster.
To re-encrypt an encrypted disk
1

Open PGP Desktop and select the disk you want to re-encrypt.

Select Disk > Re-Encrypt Disk.

Enter the password or passphrase of the encrypted disk, then click OK. The
re-encryption process begins.

Backing Up and Restoring
While most modern backup programs have no problem backing up the data on a PGP
Desktop-encrypted disk, some other backup programs do have problems with it. These
other backup programs fail when they encounter the file PGPWDE01, a file used by PGP
Desktop. The solution is to have these programs exclude PGPWDE01 from the backup
(most backup programs let you exclude individual files). Once you get your backups
working again with these programs, it is a good idea to test the backup to make sure it
works.

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Protecting Disks with PGP Whole Disk Encryption
Using PGP WDE in a PGP Universal Server-Managed Environment

Using Automatic Backup Software on an Encrypted Disk
You can automatically back up any disk this is protected with PGP Desktop. Files the
software backs up will be decrypted before being backed up.
For example, backups made using Time Machine, the automatic backup software built
into Mac OS X 10.5 (Leopard), are made normally, and the files in the backup are not
encrypted.
Note: Data recovery software (such as the Mac OS X version of Boomerang Data
Recovery) attempts to recover data from a hard drive that is not currently accessible.
If data recovery software is used on a disk that is protected with PGP Desktop, it will
find encrypted data that is not in a usable form.

Uninstalling PGP Desktop from Encrypted Disks
If you have any disks on your system that are protected by PGP Desktop, these disks
become inaccessible once PGP Desktop is uninstalled. For that reason, a safety feature
prevents you from uninstalling PGP Desktop if your system has any disks that are
encrypted by PGP WDE. In this instance you see an error message explaining that the
uninstall process is being terminated to protect the encrypted disk.
If you want to uninstall PGP Desktop, first decrypt any disks on your system that are
protected using PGP Desktop.
To uninstall PGP Desktop
•

Open PGP Desktop and select PGP > Uninstall.

Using PGP WDE in a PGP Universal Server-Managed
Environment
The PGP Whole Disk Encryption feature can be administered for PGP Desktop users in a
PGP Universal Server-managed environment. Administrators can deploy PGP Desktop
installers to users throughout their enterprise.

PGP Whole Disk Encryption Administration
The PGP administrator can control:
•

Whether or not the PGP Whole Disk Encryption feature is available to users. If
you are in a PGP Universal-managed environment and the PGP Whole Disk
Encryption feature is not available, check with your PGP administrator to see if the
feature has been disabled by policy.

Protecting Disks with PGP Whole Disk Encryption
Using PGP WDE in a PGP Universal Server-Managed Environment

The PGP Whole Disk Encryption feature also requires an appropriate license from
Symantec Corporation. If the feature is disabled for you, even though it is enabled
by policy, check with your PGP administrator to make sure you have an
appropriate license.
•

Whether or not you can recover disks that are protected with PGP Whole Disk
Encryption. If you forget the passphrase to a disk encrypted with PGP Whole Disk
Encryption, the disk is not accessible. However, if you are using the PGP Whole
Disk Encryption feature in a PGP Universal Server-managed environment, check
with your PGP administrator to see if disk recovery is an available option.

•

Whether or not your boot disk must be encrypted with PGP Whole Disk
Encryption when you install PGP Desktop.
If you are using PGP Desktop in a PGP Universal Server-managed environment,
contact your PGP administrator for more information.

If your policy should change from one to the other, specifically from having the ability
to encrypt a disk to having that feature disabled, note that you are still able to use any
drives that are already whole disk encrypted. You will not, however, be able to encrypt
any more drives, re-encrypt existing encrypted drives, or add new users.

Creating a Recovery Token
If you are working within a PGP Universal Server-managed environment, and the policy
that applies to you allows for the creation of whole disk recovery tokens, then PGP
Desktop creates a recovery token whenever you encrypt a disk, partition (on Windows
systems), or removable disk with PGP Whole Disk Encryption. This recovery token can
be used to access the disk or partition (on Windows systems) in case the passphrase or
authentication token (on Windows systems) is lost.
If the policy that applies to you does not support it, or if you are not in a PGP Universal
Server-managed environment with a pre-configured installation of PGP Desktop, you
will not be able to use whole disk recovery tokens.
This recovery token is automatically sent to the PGP Universal Server managing
security for the disk or partition (on Windows systems) protected by PGP Whole Disk
Encryption.
If you are in a PGP Universal Server-managed environment, and you lose the
passphrase or authentication token used to protect a disk or partition (on Windows
systems) with PGP Whole Disk Encryption, you should contact your PGP administrator
for assistance using the recovery token.
The recovery token can be used only once to gain access to a disk or partition (on
Windows systems) that has been protected using PGP Whole Disk Encryption. After a
recovery token is used, a new one is generated automatically and sent to the PGP
Universal server. The PGP Desktop user is given the option of creating a new user, or
keeping the existing one(s) on the disk or partition.
Note that the recovery token is used only to gain access to an encrypted disk or
partition (on Windows systems). You cannot use the recovery token to encrypt or
decrypt data.

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Protecting Disks with PGP Whole Disk Encryption
Recovering Data From an Encrypted Drive

Caution: Consider re-encrypting disks or partitions (on Windows systems) protected
by PGP Whole Disk Encryption if security is compromised, by passphrase exposure
for example, or loss of the authentication token (on Windows systems). This process
re-encrypts the disk or partition with the same encryption algorithm, but with a
different underlying encryption key. The result is as if you decrypted the disk or
partition and encrypted it again, but is much faster.

Using a Recovery Token
Once you have received the recovery token from your PGP Universal Administrator,
follow the steps below to unlock your disk.
When you enter a recovery token, you do not need to match the case (all uppercase) or
dashes that you received from your PGP Universal Administrator. You can enter all
lowercase characters without the dashes if you want.
To use a recovery token on a boot disk
•

At the PGP BootGuard screen, enter the recovery token in the passphrase field.

To use a recovery token on a removable drive
•

Insert the disk and enter the recovery token when prompted to enter the
passphrase.

Recovering Data From an Encrypted Drive
Although rare, you may find it necessary to recover data from an encrypted drive that
has been damaged or corrupted. Or, you may find that you do not have the login
information in order to access a drive (such as a former employee's encrypted drive).
In these cases, there are several things you can do:
1

Use a recovery disk. If a recovery disk was created before the disk or partition
was encrypted, you can use it to decrypt the disk. For more information, see
Creating and Using Recovery Disks (on page 132).

Use another system to decrypt the drive. If your Macintosh has a FireWire port
and supports FireWire Target Disk Mode, you can connect your Macintosh to
another system that has PGP Desktop or PGP Desktop for Mac OS X installed on it.

Use the Whole Disk Recovery Token. If you are using PGP Desktop in a PGP
Universal Server-managed environment, the recovery token is created
automatically when the disk is encrypted. For more information, see Using a
Recovery Token (on page 131).

For more information on how to recover data, see the PGP Support KB Article 1018
https://support.pgp.com/?faq=1018.
For information on how to recover data using target disk mode, see the PGP Support KB
Article 1583 (http://support.pgp.com/?faq=1583).

Protecting Disks with PGP Whole Disk Encryption
Decrypting an Encrypted Disk

Creating and Using Recovery Disks
While the chances are extremely low that a boot.efi file could become corrupt on a boot
disk or partition protected by PGP Whole Disk Encryption, it is possible. If this occurs,
it could prevent your system from booting. Prepare for this unlikely event by creating a
recovery CD before you encrypt a boot disk or partition using PGP Desktop.
Caution: Note that recovery disks work only with the version of PGP Desktop that
created the recovery disk. For example, if you attempt to use a 10.0.0 recovery disk to
decrypt a disk protected with PGP WDE 10.2 software, it will render the PGP WDE
10.2 disk inoperable.
This section includes procedures for creating a recovery compact disc. It also discusses
their use. For more information, see PGP KB article 1658
(http://support.pgp.com/?faq=1658 ).
To create a recovery CD
1

Download and save the recovery iso image to your system.

Burn the image to a CD-ROM using the Mac OS X Disk Utility. For information on
how to do this, see the Apple Support article HT2087
(http://support.apple.com/kb/HT2087).

Remove the recovery CD from the drive and label it appropriately.

To use a recovery disc or diskette
Caution: Once you have started to decrypt a disk or partition using a recovery disc or
diskette, do not stop the decryption process. Depending on the size of the disk being
decrypted, this process can take a long time. A faster way to decrypt the drive is to
use another system that has the same version of PGP Desktop installed on it. For
more information, see Decrypting a PGP WDE-Encrypted Disk (see "Decrypting an
Encrypted Disk" on page 133).
1

Boot the Macintosh system with the disc. To boot with the disk, hold down the
Option key when rebooting the system and select to boot from the recovery disc.
The PGP BootGuard screen is displayed.

Enter your passphrase when prompted and press Enter.

To decrypt the disk, press D then press Enter.

Decrypting an Encrypted Disk
As a best practice, if you need to perform any disk recovery activities on a disk
protected with PGP Desktop, Symantec Corporation recommends that you first decrypt
the disk. Decrypt a disk by doing one of the following:
•

Use the Disk > Decrypt option in PGP Desktop (see the following procedure for
information on how to use this option to decrypt a disk).

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Protecting Disks with PGP Whole Disk Encryption
Moving Removable Disks to Other Systems

•

Connect a removable disk to a second system and decrypt from that system's
software. If the removable disk is formatted as a FAT drive, you can decrypt it
using PGP Desktop version 10.1 for Windows or Mac OS X, or PGP Desktop 10.2 for
Mac OS X. If the disk is formatted as an HFS drive, you must use PGP Desktop for
Mac OS X.

Once the disk is decrypted, proceed with your recovery activities.
To decrypt a disk
1

Open PGP Desktop, and select Disk > Decrypt.

Enter the password to unlock the disk and click OK.
The time it will take to decrypt the disk is displayed in the PGP Desktop window.
To pause or cancel the decryption process, click Stop.

Moving Removable Disks to Other Systems
You can move removable Windows-formatted disks to another Mac OS X system that
has PGP Desktop 10.2 installed, and access the encrypted files on the other system.
You must be able to authenticate to access the contents of the disk.
Note: To protect a disk using the PGP Whole Disk Encryption feature, you must have
the appropriate PGP Desktop license. However, if you have protected a removable
Windows-formatted disk with PGP Whole Disk Encryption, you can use that
removable disk on another computer with PGP Desktop 10.2 installed—even if the
other system does not have a PGP Desktop license that supports PGP Whole Disk
Encryption.

Accessing Data on Encrypted Removable Disks
If you use PGP Whole Disk Encryption for Windows to protect a removable disk—a USB
flash disk, for example—you can move that disk to another Windows or Mac OS X
system and access the encrypted files on that flash disk on the other system. Removable
disks created using PGP WDE on Linux can be accessed using PGP Desktop version 10.0
or later only.
You will need to be able to authenticate to access the contents of the disk.
Note: Consider PGP Desktop licensing when moving an encrypted, removable disk.
To protect a disk using the PGP Whole Disk Encryption feature, you must have the
appropriate PGP Desktop license. However, if you have protected a removable disk
with PGP Whole Disk Encryption, you can use that removable disk on another
computer with PGP Desktop 9.5.2 or later installed—even if the other system does
not have a PGP Desktop license that supports Whole Disk Encryption.

Protecting Disks with PGP Whole Disk Encryption
Special Security Precautions Taken by PGP Desktop

Special Security Precautions Taken by PGP Desktop
PGP Desktop has features that help avoid security problems with the PGP Whole Disk
Encryption feature. These precautions also apply to PGP Virtual Disk volumes.

Passphrase Erasure
When you enter a passphrase, PGP Desktop uses it only for a brief time, then erases it
from memory. PGP Desktop also avoids making copies of the passphrase. The result is
that your passphrase typically remains in memory for only a fraction of a second.
Without this critically important feature, someone could search for your passphrase in
your computer memory while you were away from the system. You would not know it,
but they would then have full access to data protected by this passphrase.

Virtual Memory Protection
Your passphrase or other keys could be written to disk as part of the virtual memory
system swapping memory to disk. PGP Desktop takes care that the passphrases and
keys are never written to disk. This feature prevents a potential intruder from scanning
the virtual memory file looking for passphrases.

Memory Static Ion Migration Protection
When you protect a disk or partition (on Windows systems) with PGP Whole Disk
Encryption, your passphrase is turned into a key. This key is used to encrypt and
decrypt the data on the encrypted disk or partition. While the passphrase is erased
from memory immediately, the key (from which your passphrase cannot be derived)
remains in memory.
This key is protected from virtual memory; however, if a certain section of memory
stores the exact same data for extremely long periods of time without being turned off
or reset, that memory tends to retain a static charge, which could be read by attackers.
If your encrypted disk or partition (on Windows systems) is decrypted for long periods,
over time, detectable traces of your key could be retained in memory. Devices exist that
could recover the key. You won’t find such devices at your neighborhood electronics
shop, but major governments are likely to have a few.
PGP Desktop protects against this by keeping two copies of the key in RAM, one normal
copy and one bit-inverted copy, and inverting both copies every few seconds.

Other Security Considerations
In general, the ability to protect your data depends on the precautions you take, and no
encryption program can protect you from sloppy security practices. For instance, if you
leave your computer on with sensitive files open when you leave your desk, anyone can
access that information—even if the disk or partition (on Windows systems) is protected
using PGP Whole Disk Encryption.
Here are some tips for maintaining optimal security:

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Protecting Disks with PGP Whole Disk Encryption
Technical Details About Encrypting Boot Disks

•

When you are away from your desk, use a screen saver with a password to deter
others from accessing your computer or viewing your screen.

•

Make sure that your encrypted disks or partitions (on Windows systems) are not
available to other computers on a network. You may need to arrange this with the
network management staff within your organization. Once you have decrypted
your disk or partition, PGP Whole Disk Encryption can no longer protect the files.
They can be seen by anyone with network access to them. Consider the PGP
Virtual Disk feature for storing files that need to be locked even while you are
using your computer.

•

Never write down your passphrase. Pick something you can remember. If you have
trouble remembering your passphrase, use something to jog your memory, such as
a poster, a song, a poem, or a joke—just do not write it down.

•

If you use PGP Desktop at home and share your computer with other people, they
will probably be able to see your open files on a disk or partition (on Windows
systems) that is protected using PGP Whole Disk Encryption. As long as you shut
down a system with a whole disk encrypted disk or partition, or if you remove an
encrypted removable disk from the system, all files on the disk or partition remain
encrypted and fully protected.

•

When you leave your computer for any length of time, Symantec Corporation
recommends that you shut down your Macintosh system, rather than putting the
system to Sleep. This ensures that no one can access your encrypted system when
returned from Sleep mode.

Technical Details About Encrypting Boot Disks
To support PGP Whole Disk Encryption of boot disks on Mac OS X, PGP Desktop creates
a new partition (using GUID Partition Table) and puts a new boot loader onto the new
partition.
Important: Versions of PGP Desktop prior to Version 10.2 supported APM partitions;
this partitioning method does not support PGP Whole Disk Encryption of boot disks,
so Version 9.9 and later use the GUID Partition Table (GPT) partitioning method.
Because of this change, all disks that are PGP whole disk encrypted using versions of
PGP Desktop prior to Version 9.9 need to be decrypted before installing Version 9.9
or above. Older PGP whole disk encrypted disks not decrypted prior to Version 9.9
being installed will not be accessible once Version 9.9 or later is installed.
The boot loader that is installed by PGP Desktop does several things: it authenticates
users attempting to boot the disk and (when authentication is successful) it calls the
Mac OS X boot loader and decrypts the files needed for normal booting of the disk. If
authentication is not successful, it does not call the Mac OS X boot loader nor decrypt
the necessary files, and thus the disk does not boot.
Caution: Apple's Boot Camp product works only when there are two partitions on the
disk: one for Mac OS X and one for Boot Camp. Because PGP Desktop adds another
partition, Boot Camp does not work on a Mac OS X system with PGP Desktop 10.2 or
later. Other virtualization software (Parallels, for example) work normally on a Mac
OS X system with PGP Desktop 10.2 or later. Symantec Corporation strongly
recommends uninstalling Apple Boot Camp before installing PGP Desktop.

Using PGP Virtual Disks

Use PGP Virtual Disks to organize your work, keep similarly named files separate, or
keep multiple versions of the same documents or programs separate.
This section describes the PGP Virtual Disk feature of PGP Desktop.
Note: If you are using PGP Desktop in a PGP Universal Server-managed
environment, your PGP Universal Server administrator may have disabled certain
features. When a feature is disabled, the control item in the left side is not displayed
and the menu and other options for that feature are not available. The graphics
included in this guide depict the default installation with all features enabled. If your
PGP Universal Server administrator has disabled this functionality, this section does
not apply to you.

In This Chapter
About PGP Virtual Disks ............................................................................................137
Creating a New PGP Virtual Disk ..............................................................................138
Viewing the Properties of a PGP Virtual Disk.........................................................141
Using a Mounted PGP Virtual Disk...........................................................................141
Working with Alternate Users ..................................................................................144
Changing User Passphrases.......................................................................................147
Deleting PGP Virtual Disks ........................................................................................147
Maintaining PGP Virtual Disks .................................................................................148
The PGP Virtual Disk Encryption Algorithms ........................................................149
Special Security Precautions Taken by PGP Virtual Disk .....................................150

Note: PGP Virtual Disks were called PGP Disks in previous versions of PGP Desktop.
The phrase PGP Disk now includes both the PGP Virtual Disk and the PGP Whole
Disk Encryption features.

About PGP Virtual Disks
A PGP Virtual Disk is an area of space, on any disk connected to your computer, which
is set aside and encrypted. PGP Virtual Disks are much like a bank vault, and are very
useful for protecting sensitive files while the rest of your computer is unlocked for
work.

138

Using PGP Virtual Disks
Creating a New PGP Virtual Disk

A PGP Virtual Disk looks and acts like an additional hard disk, although it is actually a
single file that can reside on any of your computer disks. It provides storage space for
your files—you can even install applications, or save files to a PGP Virtual Disk — but it
can also be locked at any time without affecting other parts of your computer. When
you need to use the applications or files that are stored on a PGP Virtual Disk, you can
unlock the disk and make the files accessible again.
PGP Virtual Disks are unlocked and locked by mounting and unmounting them from
your computer. PGP Desktop helps manage this operation for you.
Although you specify a size for your PGP Virtual Disk, you can also create a
dynamically-sizing disk, one that grows larger as needs require it. The size you specify
when you are creating the disk is the maximum size the disk can become.
When a PGP Virtual Disk is mounted, you can:
•

Move/copy files into or out of the mounted PGP Virtual Disk.

•

Save files to the mounted PGP Virtual Disk.

•

Install applications within the mounted PGP Virtual Disk.

Files and applications on a PGP Virtual Disk are stored encrypted. If your computer
crashes while a PGP Virtual Disk is unmounted, the contents remain safely encrypted.
When a PGP Virtual Disk is unmounted, it does not appear within Windows Explorer or
the Mac OS X Finder, and it is inaccessible to anyone without proper authentication.
It is important to remember that all your data remains secure in the encrypted file and
is only deciphered when you access one of the files. Having the data for a volume stored
in this manner makes it easy to manipulate and exchange PGP Virtual Disks with others
but it also makes it easier to lose data if the file is somehow deleted. It is wise to keep a
back up copy of these encrypted files so that the data can be recovered if something
happens to the original.
For information about the PGP options that affect PGP Virtual Disk volumes, see Disk
Options (see "Disk Preferences" on page 173).
Caution: If you are using PGP Desktop in a PGP Universal Server-managed
environment, you may be required to create a PGP Virtual Disk after installing PGP
Desktop. If so, the size, file system, and algorithm may have been specified. For more
information, see Using PGP Desktop with PGP Universal Server (on page 185).

Creating a New PGP Virtual Disk
To create a new PGP Virtual Disk
1

Open PGP Desktop and select the PGP Disk item. The PGP Disk window is
displayed.
Note: If you did not install PGP Whole Disk (an option available if you selected
Customize during the installation of PGP Desktop) with an appropriate license,
the only section displayed in this window is New Virtual Disk.

Using PGP Virtual Disks
Creating a New PGP Virtual Disk

Click New PGP Virtual Disk. The New PGP Disk screen is displayed.

In the Enter your desired PGP Disk size field, type the amount of space that you
want to reserve for the new PGP Virtual Disk. Use whole numbers, with no decimal
places. You can also use the arrows to increase or decrease the number displayed
in the field. Choose KB (Kilobytes), MB (Megabytes), or GB (Gigabytes) from the
menu.

Specify the type of authentication you want to use for the primary user of this PGP
Virtual Disk:

•

To protect your PGP Virtual Disk with your keypair, select Public Key.

•

To protect your PGP Virtual Disk with a passphrase, select Passphrase user.

To view or change the advanced options settings, select the Advanced Options
checkbox. The Automatically resize PGP Virtual Disk as necessary checkbox is
displayed, as well as the Cipher and Format menus.
Caution: The default Advanced Options settings are appropriate for most users.
Avoid changing these settings if you are unfamiliar with them.
•

Select the Automatically resize PGP Virtual Disk as necessary checkbox if
you want PGP Desktop to manage the size of the new PGP Virtual Disk
automatically. As you add or delete files, the disk size changes appropriately.

Caution: You can select (or not select) the Automatically resize PGP Virtual
Disk as necessary option only when you are creating a PGP Virtual Disk. Once
the disk is created, you can neither change a PGP Virtual Disk from a fixed disk
to a resizable one, or vice-versa.
•

From the Cipher menu, select the encryption algorithm that you would like
to use to protect your PGP Virtual Disk: AES-256 (256 bits), CAST5
(128-bits), or EME2-AES (256 bits). For more information about these
encryption algorithms, see The PGP Virtual Disk Encryption Algorithms.

•

From the Format menu, select the disk format that you would like to use
with your PGP Virtual Disk:

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Using PGP Virtual Disks
Creating a New PGP Virtual Disk

MS-DOS. Use if you intend to share this PGP Virtual Disk with someone using
PGP Desktop 10.2 for Windows.
Mac OS Extended. The default format (also the modern Mac OS file-system
format); supports large PGP Virtual Disk volumes. The minimum size is 4 MB.
The Mac OS Extended format is also called HFS+.
Mac OS Extended (Journaled). Use if Journaling is enabled on your system.
(Journaling causes a copy of everything written to disk to be written a second
time in a private area of the file system, making disk recovery easier if
necessary.)
Mac OS Extended (Case-sensitive, Journaled). Use if case-sensitive Journaling
is enabled on your system.
Mac OS Standard. For backwards compatibility with older Mac OS operating
systems. The minimum size is 512 KB.
UNIX File System. Use if you intend to share this PGP Virtual Disk volume
with someone using a UNIX file system. The minimum size is 128 KB.
You can see format of an existing Mac OS X drive by selecting the drive, then
selecting Get Info from the File menu.
6

Click Continue.

The next step depends on whether you chose public key or passphrase
authentication.
•

For public key access, the Select a Public Key to Secure Your PGP Disk screen
is displayed, displaying the public keys you can use for authenticating to the
PGP Virtual Disk that you are creating.
Select a key from the list, then click Continue. You are prompted for the
passphrase of the key you selected (unless the passphrase is already cached, in
which case this step is skipped).
Enter the appropriate passphrase, then click OK. The Save As dialog box is
displayed. Continue with the next step.

•

For passphrase access, the Set a Master Passphrase For Your PGP Disk
screen is displayed.
In the Name field, type the name that you would like to assign to the primary
PGP Virtual Disk user (or administrator).
In the Enter your passphrase field, type the passphrase that you would like to
use. The Passphrase Quality bar indicates the strength of the passphrase that
you have typed. Select the Show Keystrokes checkbox to see the characters
that you are typing, and if you are certain that no one else can see what you are
typing.
In the Confirm your passphrase field, re-type the passphrase that you would
like to use. Click Continue. The Save As dialog box is displayed. Continue with
the next step.

Select a file name and location for the PGP Virtual Disk, then click Save.

Review the information on the PGP Disk Creation Summary screen. This screen
displays the size of the PGP Virtual Disk, the volume name and location, the
format, and so on. When you are finished, click Create.

The Creating your PGP Virtual Disk screen is displayed, showing you progress as
your PGP Virtual Disk is created. Once the disk is created, the Congratulations
screen is displayed. Click Finish.

Using PGP Virtual Disks
Viewing the Properties of a PGP Virtual Disk

Your new PGP Virtual Disk is mounted automatically, and information about it is
displayed in a Finder window. The name of the disk also is displayed under the
PGP Disk item.

Viewing the Properties of a PGP Virtual Disk
Once a PGP Virtual Disk has been created, information about the disk and settings you
can change are accessible from the Disk Properties screen.
To view the properties of a PGP Disk volume
•

Click on the name of the disk in the PGP Disk item. The Disk Properties screen is
displayed.

Using a Mounted PGP Virtual Disk
Create, copy, move, and delete files and folders on a PGP Virtual Disk just as you
normally do with any other disk on your system.
Anyone else who has access to the volume (either on the same computer or over the
network) can also access the data stored there. It is not until you unmount the volume
that the data is protected.
Caution: Although each PGP Virtual Disk file is encrypted and cannot be accessed by
anyone without proper authorization, it can still be deleted from your system.
Anyone with access to your system could delete the encrypted file containing the
PGP Virtual Disk. For this reason, keeping a backup copy of the encrypted file is an
excellent safety measure, as is keeping your computer locked when you are not
nearby.

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Using PGP Virtual Disks
Using a Mounted PGP Virtual Disk

Mounting a PGP Virtual Disk
When you create a new PGP Virtual Disk, it is automatically mounted so you can begin
using it to store your files.
To secure the contents of a volume, you must unmount it. Once a volume is unmounted,
its contents remain secured in an encrypted file where they are inaccessible until the
volume is mounted once again.
There are several ways to mount a PGP Virtual Disk:
•

In PGP Desktop, select the PGP Virtual Disk you want to mount and select Disk >
Mount.

•

In PGP Desktop, select the PGP Virtual Disk you want to mount and then click
Mount in the upper-right corner on Windows systems, or the Mount icon on the
toolbar on Mac OS X systems.

•

Change the properties of the PGP Virtual Disk so that it mounts when your
computer starts.

On Windows systems only:
•

During creation of the PGP Virtual Disk, select the Mount at Startup checkbox.
The volume mounts automatically when you start Windows. If you do not select
this during creation of the PGP Virtual Disk, you can set it as an option later.

•

In Windows Explorer, right-click the PGP Virtual Disk file, and select PGP >
Mount PGP Virtual Disk from the shortcut menu.

Mounted PGP Virtual Disk volumes appear as empty drives in Windows Explorer and
Mac OS X Finder.

Unmounting a PGP Virtual Disk
You lock a PGP Virtual Disk by unmounting it. Once a PGP Virtual Disk is unmounted,
its contents are locked in the encrypted file associated with the volume. Its contents are
inaccessible until the volume is mounted once again.
Caution: You may lose data if you unmount a PGP Virtual Disk when some files that it
contains are open. Specify options for unmounting disks by selecting PGP >
Preferences and clicking the Disk icon. One option is Allow PGP Virtual Disks to
unmount even while files are still open. If that option is selected, the option for
Don’t ask before unmounting also becomes available. Do not use these options
unless you are familiar with them. While these options can be useful for advanced
users who protect their data with regular data backups, they are not recommended
for most users.
There are several ways to unmount a PGP Virtual Disk volume:
•

In PGP Desktop, select the PGP Virtual Disk you want to unmount under the PGP
Disk item and select Disk > Unmount or click the Unmount Disk icon on the
toolbar.

•

Drag the icon of the mounted PGP Virtual Disk volume to the Trash.

Using PGP Virtual Disks
Using a Mounted PGP Virtual Disk

Set Mount Location
You can specify where the PGP Virtual Disk is mounted (located).
To set the mount location
1

Select the PGP Disk control box, then select the PGP Virtual Disk for which you
want to set the mount location.

Click Set Mount Location. The Set your PGP Disk’s mount point dialog box is
displayed.

Select one of the following:

•

Desktop (Default). Select this option to mount your PGP Disk volume on the
Desktop. This is where the PGP Virtual Disk is mounted if you do not specify
another location.

•

At the following location. Select this option to mount your PGP Virtual Disk
at a location that you specify. Click Browse, then navigate to the location at
which you would like your PGP Virtual Disk mounted. Click Open to confirm
your choice.

Click OK. The mount location for your PGP Virtual Disk is established.

Compacting a PGP Virtual Disk
To free up additional space on your PGP Virtual Disk, compact the disk. If the PGP
Virtual Disk is mounted, you must unmount the disk first, before you can compact it.
To compact a PGP Virtual Disk
•

Do one of the following:
•

In PGP Desktop, click the PGP Disk item on the left pane of the PGP Desktop
main screen, select the PGP Virtual Disk you want to compact, and then
select Disk > Compact Disk. You can also Ctrl+click (or right-click, if you
have a two-button mouse) the PGP Virtual Disk in the PGP Disk control box
and select Compact from the shortcut menu.

•

If you are using Mac OS X 10.5, in the Finder, navigate to the location of the
virtual disk file. Right-click the file and select More > PGP > Compact.
If you do not know where the PGP Virtual Disk is located, in PGP Desktop,
right-click the name of the disk and select Reveal in Finder.

Re-Encrypting PGP Virtual Disks
You can re-encrypt all data stored on a PGP Virtual Disk. You might do this for either
(or both) of two reasons:
•

You want to change the encryption algorithm currently being used to protect the
volume.

•

You suspect there has been a security breach.

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Using PGP Virtual Disks
Working with Alternate Users

With re-encryption, you encrypt your PGP Virtual Disk again, but use a different
underlying encryption key.
Caution: Adept users may be able to search the memory of a computer for the
underlying encryption key of a PGP Virtual Disk. These users could use the key to
access the volume even after being removed from the user list. Re-encrypting the
disk changes this underlying key and prevents this kind of intrusion.
To re-encrypt a PGP Virtual Disk
1

Select the PGP Disk item on the left pane of the PGP Desktop main screen, then
select the PGP Virtual Disk that you want to re-encrypt.

If the PGP Virtual Disk is mounted, unmount it.

Click Re-Encrypt. A confirmation dialog box is displayed.

Review the information it contains, then click Re-Encrypt. The Enter PGP
Passphrase dialog box is displayed.

Type the passphrase for the PGP Virtual Disk administrator, then click OK. The
PGP Virtual Disk is re-encrypted. A progress bar is displayed during the process.

When the current status displays Done, click Next.

Click Finish to complete the re-encryption process.

Working with Alternate Users
This section describes how to add, delete, and disable alternate user accounts for your
PGP Virtual Disks. Also included is information on how to change the rights for users,
including granting administrator rights to a user.

Adding Alternate User Accounts to a PGP Virtual Disk
The administrator of a PGP Virtual Disk can make it available to other users. Those
users can access the volume using their passphrases or private keys.
To add alternate user accounts to a PGP Virtual Disk
1

Click the PGP Disk item on the left pane of the PGP Desktop main window, then
select the name of the PGP Virtual Disk to which you want to add an alternate
user.

Click the plus sign icon under the User Access list of the Disk Properties screen;
select Add Public Key User or Add Passphrase User, depending on what kind of
alternate user account you want to add.
•

If you clicked Add Public Key User, select the public key of the alternate
user you want to add by dragging their key from the Key Source column to
the Keys to Add column. You can add multiple alternate users if you like.

Using PGP Virtual Disks
Working with Alternate Users

•

If you clicked Add Passphrase User, select the public key of the alternate
user you want to add by dragging their key from the Key Source column to
the Keys to Add column. The Add a user to your PGP Disk dialog box is
displayed.
In the Name field, type a name for the alternate user you are adding.
In the Enter a passphrase for this user field, type a passphrase for the user.
In the Confirm user’s passphrase field, re-type the passphrase. The
Passphrase Quality bar indicates the strength of the passphrase that you have
typed. Select the Show Keystrokes check box if you want to see the characters
you are typing.

Click OK. The Disk Properties screen is displayed again; the alternate public-key
user or alternate passphrase user is displayed in the B list.

Deleting Alternate User Accounts From a PGP Virtual Disk
At some point you may want to remove the ability of an alternate user to access a PGP
Virtual Disk.
To remove an alternate user account from a PGP Virtual Disk
1

Click the PGP Disk item on the left pane of the PGP Desktop main screen, then
select the PGP Virtual Disk for the user account you want to delete.

In the User Access list, select the name of the alternate user whose account you
want to remove. You cannot remove the Administrator.

Click the minus sign icon under the User Access list. A confirmation dialog box is
displayed.

Click Remove. The alternate user is deleted.

Disabling and Enabling Alternate User Accounts
To prevent access to a PGP Virtual Disk for an alternate user without deleting their
account entirely, you can instead temporarily disable their access.
To disable or enable an alternate user account from a PGP Virtual Disk
1

Click the PGP Disk item on the left pane of the PGP Desktop main screen, then
select the PGP Virtual Disk for the user account you want to change.

In the User Access list, select the alternate user you want to disable or enable. You
cannot disable the Administrator.

Do one of the following:
•

To disable a user, select Disk > Disable User. A confirmation dialog box is
displayed. Click Disabled. The alternate user is disabled. The user is greyed
out in the User Access list.

•

To enable a user that you previously disabled, select Disk > Enable User. The
alternate user is enabled.

145

146

Using PGP Virtual Disks
Working with Alternate Users

Changing Read/Write and Read-Only Status
Users of a PGP Virtual Disk can have either full read/write privileges, or read privileges
only. You can change these privileges for a user at any time.
To change the rights for a user of a PGP Virtual Disk
1

Click the PGP Disk item on the left pane of the PGP Desktop main screen, then
select the PGP Virtual Disk for the user account you want to change.

In the User Access list, select the name of the alternate user whose read/write
status you want to change.

Do one of the following:
•

To change the user to read-only access, Ctrl+click (or right-click) the user's
name and select Set Read-Only Access.

•

To change the user to read/write access, Ctrl+click (or right-click) the user's
name and select Allow Write Access.

Tip: These options are also available from the Disk menu when the user is
selected.
4

The rights of the selected user are changed.

Granting Administrator Status to an Alternate User
You can change the status of a user account from alternate to administrator.
To grant administrator status
1

Click the PGP Disk item on the left pane of the PGP Desktop main screen, then
select the PGP Virtual Disk for the user account you want to change.

In the User Access list, select the user you want to make administrator of the PGP
Virtual Disk. Select either a passphrase user or yourself (if you are not the current
administrator). Note that you cannot make a public key user an administrator of
the PGP Virtual Disk.

Ctrl+click (or right-click if you have a two-button mouse) and select Set as Disk
Administrator from the shortcut menu. The Enter PGP Passphrase dialog box is
displayed.
Tip: You can also select Disk > Set as Disk Administrator.

Type the passphrase for the PGP Virtual Disk administrator, then click OK. The
selected user account is changed to administrator.
Note: You can grant Administrator status to only one user account at a time. By
granting Administrator status to one account, you also remove it from another.

Using PGP Virtual Disks
Changing User Passphrases

Changing User Passphrases
To change a user passphrase for a PGP Virtual Disk
1

Select the PGP Disk control box on the left pane of the PGP Desktop main screen,
then select the PGP Virtual Disk on which you are a user.

Select the name of a passphrase user from the User Access list, then select Change
User Passphrase from the Disk menu. The Enter PGP Passphrase dialog box is
displayed.
Tip: You can also Ctrl+click (or right-click if you have a two-button mouse) the
user's name and select Change User Passphrase from the shortcut menu.

Type the passphrase for the PGP Virtual Disk administrator, then click OK.

Type a new passphrase, type the passphrase again to confirm it, and click OK. The
passphrase is changed.

Deleting PGP Virtual Disks
At some point you may decide you no longer need a particular PGP Virtual Disk and
may choose to delete the disk entirely.
Caution: When you delete a PGP Virtual Disk, all data on it is also deleted. There is no
way to retrieve the data once you delete a PGP Virtual Disk. Make sure that you have
copied any data that you want to save to another location before deleting a PGP
Virtual Disk.
Make sure the selected PGP Virtual Disk is not mounted. You cannot delete the PGP
Virtual Disk if the volume is mounted.
To delete a PGP Virtual Disk
1

Select the PGP Disk control box on the left pane of the PGP Desktop main screen,
then select the PGP Virtual Disk you want to delete.

Select Reveal in Finder from the shortcut menu. A Finder window is displayed
with the PGP Virtual Disk file selected. If you have opted to have Mac OS X display
file extensions, the PGP Virtual Disk is a .pgd file.

Drag the file to the Trash, then select Empty Trash from the File menu in the
Finder.

In PGP Desktop, Ctrl+click (or right-click if you have a two-button mouse) the PGP
Disk volume you want to delete and select Remove Item from the shortcut menu.
The PGP Disk is deleted from your system, as well as from PGP Desktop.

147

148

Using PGP Virtual Disks
Maintaining PGP Virtual Disks

Maintaining PGP Virtual Disks
This section describes how to take proper care of the PGP Virtual Disk that you use with
your computer.

Mounting PGP Virtual Disk Volumes on a Remote Server
You can place PGP Virtual Disk volumes on any kind of server (Windows or UNIX). The
volumes can then be mounted by anyone with a Windows computer and PGP Desktop.
Note: The first person to mount the PGP Virtual Disk volume locally has read-write
access to the volume. No one else is then able to access the volume. If you want
others to be able to access files within the volume, you must mount the volume in
read-only mode (applies to FAT and FAT32 file system formats only). All users of the
volume then have read-only access.
If the PGP Virtual Disk volume is stored on a Windows server, you can also mount the
volume remotely on the server and allow people to share the mounted volume.
However, this action provides no security for the files within the volume.

Backing up PGP Virtual Disk Volumes
Backing up the contents of your PGP Virtual Disk is the best way to safeguard your
information from hardware failure or other loss.
It is not advisable to back up the contents of a mounted (and therefore, decrypted) PGP
Virtual Disk just as you would any other volume. The contents are not encrypted, and
are accessible to anyone who can restore the backup. Instead, instead make a backup
copy of the encrypted volume.
To back up PGP Virtual Disks in encrypted form
1

Unmount the PGP Virtual Disk.

In the Finder, locate the PGP Virtual Disk file. If you have opted to have Mac OS X
display file extensions, the PGP Virtual Disk file name ends with .pgd.
Tip: You can find the PGP Virtual Disk file easily by Ctrl+clicking (or
right-clicking if you have a two-button mouse) the disk in the PGP Disk of the
PGP Desktop side panel. Select Reveal in Finder from the shortcut menu.

Copy the unmounted encrypted PGP Virtual Disk file to a CD, DVD, tape,
removable cartridge, or diskette just as you would any other file.

Even if some unauthorized person has access to the backup, they cannot decipher its
contents.
When making backups of encrypted PGP Virtual Disk files, keep these issues in mind:
•

Backing up encrypted files to a network drive gives others plenty of opportunity to
guess at a weak passphrase. It is much safer to back up only to devices over which
you have physical control.

Using PGP Virtual Disks
The PGP Virtual Disk Encryption Algorithms

•

A lengthy, complicated passphrase helps further improve the security of your
data.

•

If you are on a network, make sure that any network back up system does not back
up the files from your mounted PGP Virtual Disk. (You may need to discuss this
with your System Administrator.) Once a PGP Virtual Disk is mounted, its files are
decrypted and can be copied to a network backup system that vulnerable state.

Exchanging PGP Virtual Disks
You can exchange PGP Virtual Disk with other users who have PGP Desktop installed
on their computers. You do that by sending them a copy of the PGP Virtual Disk data
file, which contains the volume data. Here are some of the ways you might exchange
PGP Virtual Disk:
•

As mail attachments

•

On a removable disk or CD

•

Over a network

Once the other user has the PGP Virtual Disk file, they can mount it on a system
running PGP Desktop and use the correct passphrase to access it. If the volume was
encrypted to their public key, they would use their private key for access.
Note: Public key is the most secure protection method when adding alternate users
to a PGP Virtual Disk because: (1) You do not need to exchange a passphrase with the
alternate user which, depending on your method, could be intercepted or overheard.
(2) The alternate user does not need to memorize another passphrase which could be
forgotten. (3) It is easier to manage a list of alternate users if each uses their own
private key to unlock the volume.

The PGP Virtual Disk Encryption Algorithms
Encryption employs a mathematical formula to scramble your data so that no one else
can use it. When you apply the correct mathematical key, you unscramble the data. The
PGP Virtual Disk volume encryption formula uses random data for part of the
encryption process.
The PGP Desktop application offers strong algorithm options for protecting your PGP
Virtual Disk volumes: AES-256, CAST, and Twofish.
•

The Advanced Encryption Standard (AES) is the NIST-approved encryption
standard. The underlying cipher is Rijndael, a block cipher designed by Joan
Daemen and Vincent Rijmen. The AES replaces the previous standard, the Data
Encryption Standard (DES). PGP Virtual Disk volumes can be protected with the
strongest variation of AES, AES-256 (that is, AES with a key size of 256 bits).

•

CAST is considered an excellent block cipher because it is fast and very difficult to
break. Its name is derived from the initials of its designers, Carlisle Adams and
Stafford Tavares of Northern Telecom (Nortel). Nortel has applied for a patent for
CAST, but they have made a commitment to make CAST available to anyone on a
royalty-free basis. CAST appears to be exceptionally well-designed by people with
good reputations in the field.

149

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Using PGP Virtual Disks
Special Security Precautions Taken by PGP Virtual Disk

The design is based on a very formal approach, with a number of formally
provable assertions that give good reasons to believe that it probably requires key
exhaustion to break its 128-bit key. CAST has no weak keys. There are strong
arguments that CAST is immune to both linear and differential cryptanalysis, the
two most powerful forms of cryptanalysis in the published literature, both of
which have been effective in cracking the Data Encryption Standard (DES).
EME2-AES (256 bits) is a stronger algorithm that encrypts twice for each
operation. EME2 (Encrypt-Mix-Encrypt v2) is a wide block mode algorithm that is
currently under review by the IEEE Standards Working Group.

Special Security Precautions Taken by PGP Virtual Disk
PGP Desktop takes special care to avoid security problems with PGP Virtual Disk
volumes that other programs may not.
These precautions also apply to whole disk encrypted drives.

Memory Static Ion Migration Protection
When you mount a PGP Virtual Disk volume, your passphrase is turned into a key. This
key is used to encrypt and decrypt the data on your PGP Virtual Disk volume. While the
passphrase is erased from memory immediately, the key (from which your passphrase
cannot be derived) remains in memory while the disk is mounted.
This key is protected from virtual memory; however, if a certain section of memory
stores the exact same data for extremely long periods of time without being turned off
or reset, that memory tends to retain a static charge, which could be read by attackers.
If your PGP Virtual Disk volume is mounted for long periods, over time, detectable
traces of your key could be retained in memory. Devices exist that could recover the
key. You won’t find such devices at your neighborhood electronics shop, but major
governments are likely to have a few.
PGP Desktop protects against this by keeping two copies of the key in RAM, one normal
copy and one bit-inverted copy, and inverting both copies every few seconds.

Using PGP Virtual Disks
Special Security Precautions Taken by PGP Virtual Disk

Other Security Considerations
In general, the ability to protect your data depends on the precautions you take, and no
encryption program can protect you from sloppy security practices. For instance, if you
leave your computer running with sensitive files open when you leave your desk,
anyone can access that information or even obtain the key used to access the data.
Here are some tips for maintaining optimal security:
•

Unmount PGP Virtual Disk volumes when you leave your computer. This way, the
contents will be safely stored in the encrypted file associated with the volume
until you are ready to access it again.

•

Use a screen saver with a password so that it is more difficult for someone to
access your computer or view your screen when you are away from your desk.

•

Make sure that your PGP Virtual Disk volumes cannot be seen by other computers
on the network. You may need to talk to your network management people to
guarantee this. The files in a mounted PGP Virtual Disk volume can be accessed by
anyone who can see them on the network.

•

Never write down your passphrases. Pick something you can remember. If you
have trouble remembering your passphrase, use something to jog your memory,
such as a poster, a song, a poem, a joke, but do not write down your passphrases.

•

If you use PGP Desktop at home and share your computer with other people, they
will probably be able to see your PGP Virtual Disk volume files. As long as you
unmount the PGP Virtual Disk volumes when you finish using them, no one else
will be able to read their contents.

•

If another user has physical access to your computer, that person can delete your
PGP Virtual Disk files as well as any other files or volumes. If physical access is an
issue, try either backing up your PGP Virtual Disk files or keeping them on an
external device over which only you have physical control.

•

Be aware that copies of your PGP Virtual Disk volume use the same underlying
encryption key as the original. If you exchange a copy of your volume with another
and both change your master passwords, both of you are still using the same key
to encrypt the data. While it is not a trivial operation to recover the key, it is not
impossible.
You can change the underlying key by re-encrypting the volume.

151

Accessing Mobile Data with PGP
Portable
Use PGP Portable to distribute encrypted files to users who do not have PGP Desktop
software. Use PGP Portable to transport files securely to other systems that do not or
cannot have PGP software installed.
PGP Portable provides:
•

Portability of secured documents

•

Ease of distribution of secured documents

There are two types of users of PGP Portable: the user who creates the PGP Portable
Disk containing secured data, and the user who does not have PGP software but needs
to access that secured data. You might also be both types of users: creating a PGP
Portable Disk that you can take and use on a computer at a customer's site, for example.
On a Mac OS X system, you can access encrypted data that is stored on a PGP Portable
Disk.

In This Chapter
Accessing Data on a PGP Portable Disk................................................................... 153

Accessing Data on a PGP Portable Disk
The contents of a PGP Portable Disk can be accessed in three ways:
•

By mounting the CD, DVD, or removable USB drive on a Windows system, and
running the PGP Portable Disk application (which launches automatically if
autorun is enabled).

•

By mounting the CD, DVD, or removable USB drive on a Mac OS X system, and
running the PGP Portable Disk application.

When you access data on a PGP Portable Disk, remember that you are actually
mounting two items: the removable device on which the PGP Portable Disk resides, and
the PGP Portable Disk itself (which is mounted as a separate item). When you are
finished, be sure to unmount the PGP Portable Disk before safely ejecting the
removable device.
The steps to access data on a PGP Portable Disk are similar for Windows and Mac OS X
systems.
Warning: Be sure that you properly unmount a removable device before physically
removing it from the system. Failure to do so may result in corrupted file contents.
T

154

Accessing Mobile Data with PGP Portable
Accessing Data on a PGP Portable Disk

To access data on a PGP Desktop Disk using a Mac OS X system
1

Insert the removable device on which the PGP Desktop Disk is located. This can be
a CD/DVD or a flash or removable drive.

Open the mounted removable device and browse for the PGP Desktop application
(PGP Portable). Double-click the application. The PGP Portable dialog box is
displayed.

Enter the passphrase for the PGP Desktop Disk.
Note: If the creator of the PGP Desktop Disk requires that the passphrase be
changed on first use, when the disk is first inserted into a drive after creation,
the dialog box that appears requires that you enter the current passphrase, and
then change and confirm the new passphrase.
When the correct passphrase has been entered, the PGP Desktop Disk is mounted.
If the PGP Desktop Disk is mounted as a read-write device, you can add data to it.
If the PGP Desktop Disk is mounted as a read-only device, you cannot add data.
Note: The volume name for the PGP Desktop Disk is unique to PGP Desktop and
may not match the name of the volume when created.

When you are finished using the PGP Desktop Disk, unmount the PGP Desktop
Disk (in the dock, click the PGP Desktop icon and then click Unmount. The drive
that was mounted for the PGP Desktop Disk is unmounted.

Properly eject the USB device or disc from your computer.
Warning: Be sure that you properly unmount a removable device before physically
removing it from the system. Failure to do so may result in corrupted file contents.

To view available disk space
•

To view available disk space and total size of the PGP Desktop Disk once the disk
has been mounted, select the PGP Desktop icon in the dock. If PGP Desktop is still
calculating the amount of free space, the message Calculating available space is
displayed.

To obtain additional information about PGP Desktop
•

To obtain more information about PGP Desktop, in the left bottom corner of the
PGP Portable dialog box, click the link for More Info. Your browser launches and
the PGP Support site page is displayed.

Accessing Mobile Data with PGP Portable
Accessing Data on a PGP Portable Disk

Changing the Passphrase for a PGP Portable Disk
There may be times when it is necessary to change the passphrase associated with a
PGP Portable Disk. Note that you cannot change the passphrase on any PGP Portable
Disk that is read-only (including PGP Portable Disks burned to CD/DVD media).
To change the passphrase on a PGP Desktop Disk using a Mac OS X system
1

Insert the removable device on which the PGP Desktop Disk is located. This can be
a CD/DVD or a flash or removable drive.

Open the removable device and locate the PGP Desktop application (PGP Portable).
Double-click the application, and enter the passphrase for the PGP Desktop Disk
when prompted. When the correct passphrase has been entered, the PGP Desktop
Disk is mounted.

Open PGP Desktop by clicking the icon in the dock and in the PGP Desktop dialog
box, clicking Change Passphrase.

Enter the current passphrase, Enter and confirm the new passphrase, and click
Change.

Unmounting a PGP Portable Disk
Be sure that you properly unmount a removable device before physically removing it
from the system. Failure to do so may result in corrupted file contents.
To unmount a PGP Portable Disk
1

Open PGP Portable. To do this, do one of the following:
•

To open PGP Portable on a Windows system, right-click the system tray icon
and choose Unmount and Exit.

•

To open PGP Portable on a Mac OS system, click the icon in the dock and
choose Unmount and Exit.

The PGP Portable Disk is unmounted.
2

Safely eject and remove the device from your system.

155

Using PGP Zip

Use PGP Zip to create, open, and edit encrypted and compressed packages, called PGP
Zip archives. This section describes how to use the PGP Zip feature of PGP Desktop.
Note: If you are using PGP Desktop in a PGP Universal Server-managed
environment, your PGP Universal Server administrator may have disabled certain
features. When a feature is disabled, the control item in the left side is not displayed
and the menu and other options for that feature are not available. The graphics
included in this guide depict the default installation with all features enabled. If your
PGP Universal Server administrator has disabled this functionality, this section does
not apply to you.

In This Chapter
Overview .......................................................................................................................157
Creating PGP Zip Archives.........................................................................................158
Opening a PGP Zip Archive........................................................................................159
Verifying Signed PGP Zip Archives ..........................................................................159

Overview
A PGP Zip Archive package is a single file that is encrypted and compressed for
convenient transport or backup. These archive files can hold any combination of files
and/or folders, and are especially convenient for secure transport or backup.
When you create a PGP Zip archive, you have the option of automatically deleting
(shredding) the original files from your system when the archive has been created.
When you receive a PGP Zip archive, choose to extract all of the files and/or folders in
the archive or just the ones you want.
Create PGP Zip archives that are:
•

Encrypted to a public key. If you are sending the PGP Zip archive to one or more
persons whose public keys you have, you should encrypt the archive to their public
keys; thus, only the intended recipients can open the archive. The recipients must
have PGP Desktop installed.

•

Encrypted to a passphrase. If you prefer to encrypt to a passphrase or you’re
sending the archive to multiple recipients, some of whom you don’t have their
public key, you can specify conventional encryption and encrypt the archive using
a passphrase. In this case, you will need to communicate the passphrase to the
recipients so they can open the archive. The recipients must have PGP Desktop
installed.

PGP Zip archives are encrypted to the preferred cipher for PGP Desktop (if configured
by a PGP administrator) or to AES256. PGP Zip Archives can be freely moved between
Mac OS X and Windows platforms. PGP Desktop must be installed on the system to
which the PGP Zip archive is being moved.

158

Using PGP Zip
Creating PGP Zip Archives

Creating PGP Zip Archives
To create a new PGP Zip archive
1

Open PGP Desktop and select the PGP Zip item. The PGP Zip screen is displayed.

Click Create new PGP Zip. The Untitled PGP Zip dialog box is displayed.

In the Files tab, specify what files and/or folders you want to be part of the PGP
Zip archive you are creating. Do this by:
•

Dragging and dropping the files/folders into the list.

•

Clicking the plus sign icon below the list, then select the files and/or folders
you want to be part of the PGP Zip archive in the dialog box displayed. Click
Add to add the files to the list.

If you add a file or folder you later decide you do not want, select the file or folder
in the list and click the minus sign icon below the list. The file or folder is removed
from the list.
4

Select Shred original files if you want to securely delete from your system the
files/folders you are putting into the PGP Zip archive.

When you have specified the files/folder you want included in the PGP Zip archive,
click the Security tab.

If desired, specify a private key from your keyring to provide a Signature for the
PGP Zip archive you are creating.
This specified private key is used to digitally sign the PGP Zip archive being
created. The recipient(s) can verify who the archive is from by verifying the digital
signature using the corresponding public key.
•

To view the properties of the selected signing key, click the Key icon to the
right of the user ID of the key. Close the Key Info dialog box when you are
done.

Select the type of encryption you want to use:
•

Encrypt with recipient keys. Use this option to encrypt the PGP Zip archive
to the public keys of the recipient(s). This ensures that only those recipient(s)
can open the archive.
If you select public-key encryption, drag and drop the public keys of the
recipients onto the list or click the plus sign icon and choose the public keys of
the desired recipients.

•

Encrypt with passphrase only. Use this option to encrypt this PGP Zip
archive to a passphrase you specify when saving the archive. Only those
persons who know the passphrase can open the archive. Remember that you
will need to communicate this passphrase to the person(s) you want to open
the PGP Zip archive.
Enter the passphrase in the Passphrase field and then again in the Confirm
field. If you want to see the passphrase as you type it, select Show Keystrokes.

Using PGP Zip
Opening a PGP Zip Archive

•

Sign Only (no encryption). Use this option to create an unencrypted PGP Zip
archive. However, because you are not encrypting the PGP Zip archive, you
must specify a signing key using the Signature field.

If you have only one file in your PGP Zip archive and you are signing the file but
not encrypting it, create a detached signature file by selecting the Save Detached
Signature File checkbox.
If you want to create a detached signature file, you can put one file only in the
archive, you must choose a signing key, and you cannot encrypt the archive.

Click Save.

Specify a file name and a location for the PGP Zip archive, then click Save. If you
specified a signing key in the Signature field, you are prompted for the passphrase
to the signing key (if it is not already cached).

Enter the appropriate passphrase, then click OK. The PGP Zip archive is created in
the location you specified.

Opening a PGP Zip Archive
PGP Desktop must be installed on the system to open a PGP Zip archive.
To open a PGP Zip archive
1

Double click the archive file and do one of the following:
•

If the archive was encrypted to your public key, you are prompted for the
passphrase to your private key, which will be used to decrypt the archive (if
the passphrase is cached, you do not need to enter it). Enter the appropriate
passphrase and click OK.

•

If the archive was encrypted to a passphrase, you are prompted for the
passphrase. Enter the appropriate passphrase and click OK.

If the archive was also signed, PGP Desktop attempts to verify the signature; when
verification is complete, a verification screen is displayed, displaying the results of
the verification process.
2

If two or more files/folders were in the archive, a new folder is created that
includes the files and/or folders that were in the PGP Zip archive.
If only one file was in the archive, just that file is created at the location of the PGP
Zip archive.

Verifying Signed PGP Zip Archives
If you received a signed PGP Zip archive, you should verify it so that you know who it
came from and that the archive was not tampered with before you got it. Files that are
not signed cannot be verified.

159

160

Using PGP Zip
Verifying Signed PGP Zip Archives

To verify a signed PGP Zip archive
1

In PGP Desktop, select View > Verification Info. The Verification Info screen is
displayed.

Drag the signed PGP Zip (.pgp) file you want verified onto the Drag Signed Files
Here box. PGP Desktop verifies the signature and displays the verification
information.

To clear the list of verified archives, click Clear. All listings on the Verification
Info screen are removed.

Shredding Files with PGP Shredder

If you want to completely destroy sensitive files without leaving fragments of their data
behind, use the PGP Shredder utility.
Note: If you are using PGP Desktop in a PGP Universal Server-managed
environment, your PGP Universal Server administrator may have disabled certain
features. When a feature is disabled, the control item in the left side is not displayed
and the menu and other options for that feature are not available. The graphics
included in this guide depict the default installation with all features enabled. If your
PGP Universal Server administrator has disabled this functionality, this section does
not apply to you.

In This Chapter
Using PGP Shredder to Permanently Delete Files and Folders............................161

Using PGP Shredder to Permanently Delete Files and
Folders
If you want to destroy sensitive files or folders completely, use the PGP Shredder
feature. When you delete files or folders using PGP Shredder, all traces of the item are
removed.
The PGP Shredder feature works by overwriting your data with random text. It repeats
this multiple times, or passes. You can set the number of passes that the PGP Shredder
feature makes whenever it deletes a file—do that by opening the Disk panel of the
Preferences screen. For more information about setting options and preferences, see
Disk Options/Preferences (see "Disk Preferences" on page 173).
The shred session can be lengthy, depending on such factors as the number of passes
you specified, the speed of the processor, and how many other applications are running.
Note: When set for three passes, PGP Shredder exceeds the media sanitization
requirements specified in the Department of Defense 5220.22-M standard. While
more passes are allowed, modern disk hardware does not require more than two
passes. Security continues to increase up to approximately 28 passes. The PGP
Shredder feature is capable of up to 49 passes, but remember that more passes
means more time needed for secure deletion.
There are multiple ways to use PGP Shredder:
•

Use the PGP Shredder icon. When PGP Desktop was installed, the PGP Shredder
feature was installed into the same directory as the PGP Desktop application.
Creating an Alias to the PGP Shredder icon, then moving the Alias to the Dock or
Desktop makes the PGP Shredder convenient and easy to use.

162

Shredding Files with PGP Shredder
Using PGP Shredder to Permanently Delete Files and Folders

•

Use the PGP Shredder icon on the PGP Toolbar. Click the PGP Shredder icon in the
Toolbar, then browse to the file/folder you want to shred.

•

Select File > Shred, then browse to the file/folder you want to shred.

•

Use the Finder shortcut menus (Ctrl+click, or right-click if you are using a
two-button mouse, the file or folder and select PGP > Shred).
Caution: Some file systems use a feature called Journaling. Apple has introduced this
feature for Mac OS Extended (HFS+) file systems in Mac OS X 10.2.2. Journaling
causes a copy of everything written to disk to be written a second time in a private
area of the file system. Thus, shredding the original file causes the original file to be
shredded while the original file data is written to another part of the disk. To avoid
this problem, do not use the Journaling feature. Journaling can be disabled using
Apple’s Disk Utility. For more information on file system journaling, see Apple
Support Technical Article 107249
(http://docs.info.apple.com/article.html?artnum=107249).
Tip: Many programs automatically save files in progress, so backup copies of the file
you deleted may exist. After you delete the primary copy of a file, Symantec
Corporation recommends that you then use the PGP Shredder feature to delete any
backup copies securely.

Shredding Files using the PGP Shredder icon
To shred a file or folder using the PGP Shredder icon
1

Locate the file or folder you want to delete securely.

Drag the file or folder onto the PGP Shredder icon. A confirmation dialog box is
displayed, asking you to confirm that you want to shred (secure delete) the listed
files and/or folders.

Click OK. The file or folder is deleted from your system securely.
Tip: Create an Alias of the PGP Shredder icon on your desktop so you can shred files
without having to locate the PGP Shredder icon in the /Applications folder. Then
move the Alias to the Desktop (or Dock).

Shredding Files using the Shred Files Icon in the PGP Desktop Toolbar
To shred a file or folder using the PGP Desktop Toolbar
1

Click the Shred Files icon in the toolbar.

Locate the file or folder you want to Shred, then click Shred. A confirmation dialog
box is displayed, asking you to confirm that you want to shred (secure delete) the
listed files and/or folders.

Click OK. The file or folder is securely deleted from your system.

Shredding Files with PGP Shredder
Using PGP Shredder to Permanently Delete Files and Folders

Shredding Files using the Shred Command from the File menu
To shred a file or folder using the Shred command
1

Select File > Shred.

Navigate to the file or folder you want to Shred, then click Shred. A confirmation
dialog box is displayed, asking you to confirm that you want to shred (secure
delete) the listed files and/or folders.

Click OK. The file or folder is securely deleted from your system.

Shredding Files in the Finder
To shred a file or folder in the Finder
1

In the Finder, locate the file or folder that you want to shred.

Ctrl+click the file or folder (or right-click it if you are using a two-button mouse)
and select PGP > Shred. A confirmation dialog box is displayed, asking you to
confirm that you want to shred (secure delete) the listed files and/or folders.

Click OK. The file or folder is securely deleted from your system.

163

Setting Preferences

PGP Desktop is configured to accommodate the needs of most users, but you can adjust
some settings to suit your requirements. This section describes the options you can set
in PGP Desktop.
Note: If you are using PGP Desktop in a PGP Universal Server-managed
environment, your PGP Universal Server administrator may have disabled certain
features. When a feature is disabled, the control item in the left side is not displayed
and the menu and other options for that feature are not available. The graphics
included in this guide depict the default installation with all features enabled. If your
PGP Universal Server administrator has disabled this functionality, this section does
not apply to you.

In This Chapter
Accessing PGP Desktop Preferences ........................................................................165
General Preferences....................................................................................................166
Keys Preferences .........................................................................................................167
Master Keys Preferences ............................................................................................169
Messaging Preferences ...............................................................................................170
Disk Preferences..........................................................................................................173
Notifications Preferences...........................................................................................174
Advanced Preferences ................................................................................................176

Accessing PGP Desktop Preferences
To access the PGP Desktop Preferences
1

Open PGP Desktop.

Select PGP > Preferences.
•

Move between different kinds of preferences by clicking the icons at the top
of the Preferences dialog box

When you are done setting preferences, click the close button (the red circle in the
upper left corner of the screen).

166

Setting Preferences
General Preferences

General Preferences
The General Preferences dialog box covers a variety of PGP Desktop settings.

The options on the General page of the Preferences dialog box are:
•

Show PGP icon in the System Menu. When enabled, the PGP Desktop icon is
displayed in the Mac OS X Menu Bar while PGP Desktop is active on the system.
The PGP Menu Bar icon provides easy access to PGP Desktop functions.
•

To remove the PGP Desktop icon from the Menu Bar, deselect the checkbox.

•

To restore the PGP Desktop icon to the Menu Bar, navigate to the General
preferences screen and select the Show PGP icon in the System Menu
checkbox.

Note: If you are using PGP Desktop in a PGP Universal Server-managed
environment, this option may be required.
Removing the PGP Desktop icon from the Menu Bar does not shut down PGP
Desktop services; they continue running.
•

To stop PGP Desktop services, press the Option key. In the Menu Bar, click
the PGP Desktop icon, then select Quit.

Note: Symantec Corporation suggests that you not stop PGP Desktop services
unless required to do so.
•

My Passphrase. Provides options to save your passphrase.
•

Save my passphrase for the current login session only. Automatically saves
your passphrase in memory until you log off your computer. This is called
caching your passphrase. If you enable this option, you are prompted for
your passphrase once per private key. You are not prompted to enter it again
for the same key until you log off your computer.

Setting Preferences
Keys Preferences

Caution: When this option is enabled, it is very important that you log off your
computer before leaving it unattended. (You can log out by selecting Log out
[your name] from the Apple menu.) If you never log off, your passphrase can
remain cached for weeks, allowing anyone to read your encrypted messages, or
encrypt messages with your key while you are away from your computer. If you
normally remain logged on to your computer for long periods of time, consider
choosing one of the other passphrase caching options.

•

Save my passphrase for X. Automatically saves your passphrase in memory
for the specified duration of time. If you enable this option, you are
prompted for your passphrase once for the initial signing or decrypting task.
You are not prompted to enter it again until the specified time has elapsed.
The three number fields are for hours, minutes, seconds, respectively. The
default setting is two minutes.

•

Do not save my passphrase. Prevents your passphrase from being stored in
memory. If you enable this option, you must enter your passphrase each time
it is needed.

•

Clear passphrase cache when computer goes to sleep. Enable this
preference to have PGP Desktop clear any saved passphrases from memory
when your computer goes into Sleep mode. (Not all computers have a Sleep
mode.)

PGP Universal Synchronization. If you are in a PGP Universal Server-managed
environment, this field displays information on when policy was last updated and
when logs were last sent.

Keys Preferences
The Keys Preferences dialog box contains settings that apply to PGP Desktop keys.

The options on the Keys page are:
•

Synchronization. These settings specify how you want keys on your keyrings
synchronized with public servers.
•

Synchronize with keyservers daily. When selected, PGP Desktop performs a
daily synchronization of the public keys on your keyring with your list of
keyservers. This list includes the PGP Global Directory.

167

168

Setting Preferences
Keys Preferences

Note: If you are using PGP Desktop in a PGP Universal Server-managed
environment, this option may be required.
If changed versions of the keys are available, they are downloaded
automatically. If the keyserver notifies PGP Desktop that a key is removed
from the keyserver, PGP Desktop disables that key on the local keyring.
If you use PGP Desktop to make a change to a public key on your keyring, that
change is not automatically uploaded from your computer to any keyserver.
You must manually upload the changed key to the desired keyserver. PGP
Desktop prompts you to upload changed keys when you quit. Otherwise, to
send the key to the keyserver, right-click the changed key, select Send To from
the shortcut menu, and then select the desired keyserver from the list.
•

Automatically lookup keys on keyservers when verifying signatures.
When this option is enabled, you can specify that PGP Desktop should search
the configured keyservers for the necessary public key if you receive an
email message signed by a private key and you do not have the
corresponding public key on your local keyring.

Note: If you are using PGP Desktop in a PGP Universal Server-managed
environment, this option is not used. Your PGP Universal Server defines whether
keys are looked up and, if found, if they are cached. Keys found in a PGP
Universal Server-managed environment are never saved to your keyring.
•

When keys are found. If the public key is found on the keyserver, there are
three options:

•

Do not save to my keyring. Any key(s) found on the configured
keyservers are used only once, to verify the signature with which you
are currently working. The key is not saved to your keyring.

•

sk to save to my keyring. Specifies that PGP Desktop should ask if you
want to save found keys to your local keyring.

•

Save keys to my keyring. Specifies that found keys are automatically
saved to your local keyring.

These options also apply to X.509 certificates included in S/MIME email
messages. If specified, PGP Desktop extracts and then imports the X.509
certificate to your keyring. If you want to encrypt email using imported
certificates, be sure to manually sign the certificate.
•

Synchronize my keys with other computers using MobileMe. (MobileMe is
Apple's new version of .Mac.) Check this box to synchronize your keys using
your MobileMe account. (You must have a valid account to use this option.)
When this option is selected, the synchronization engine runs and copies
your key files to a local cache that MobileMe uses for updating.

•

To synchronize your keys with your MobileMe account immediately,
click MobileMe. The System Preferences MobileMe panel is displayed.
Log in, click the Sync panel, select the PGP Keys item in the list, and
click Sync Now.

Backup. These settings specify when and where you want your keys backed up.
•

Backup keys upon exiting PGP Desktop. When enabled, PGP Desktop
automatically backs up your keys to the location you specify:

•

to my keyring folder (default). When selected, your keys are backed up
to the default keyring folder on your system.

Setting Preferences
Master Keys Preferences

•

to this location. When selected, your keys are backed up to the location
on your computer that you specify. Click Browse to set a location.

Master Keys Preferences
The Master Key List is a set of keys that you want added by default any time you are
selecting keys for messaging, disk encryption, and PGP Zip. This saves you the step of
dragging the keys that you regularly use into the Recipients field.

169

170

Setting Preferences
Messaging Preferences

Messaging Preferences
The Messaging Preferences panel contains settings that apply to your messaging
security. It also provides access to email and IM settings.

The Messaging preferences are:
•

Secure Email. Select the Secure Email checkbox if you want PGP Desktop to
automatically secure all your email accounts. When enabled, PGP Desktop
intercepts both incoming and outgoing email messages, and secures them based
on the appropriate policies.
Deselect the Secure Email checkbox to stop PGP Desktop from securing your
email accounts.
If you select the Secure Email checkbox, you can choose these additional options:
•

Discover new accounts. Select this checkbox if you want PGP Desktop to
monitor your email activity and automatically discover new email accounts
that you are using. It then secures messages sent using those accounts.

Note: If you are using PGP Desktop in a PGP Universal managed environment,
the use of a wildcard (*) binding causes this function to be no longer active due to
all mail services will match the binding of *. Therefore all new accounts will
automatically match policy and be created even if this option is deselected.
•

Automatically add my email addresses to my key. If you select this
checkbox, PGP Desktop automatically adds to your key the email addresses
that you use to send messages. This option is enabled by default.
Deselect this checkbox to prevent email addresses from being automatically
added to your key. This has privacy value; for example, if you want to prevent
someone from finding your email address.

•

Annotate incoming email. Select this checkbox if you want incoming email
messages to be annotated with explanatory text detailing the actions that
PGP Desktop took when processing your incoming messages. You can choose
from three annotation levels:

Setting Preferences
Messaging Preferences

•

Maximum: Verbose Annotation. Adds annotations to your incoming
email detailing every action that PGP Desktop has taken during
message processing.

•

Medium: Failures and Successes. This option is the default. Provides
annotations when there has been a processing failure, such as
unknown key, or unknown signer. The Medium setting provides
annotations for all decrypted and/or signed email, but does not list
individual attached files.

•

Minimum: Failures Only. Only provides annotations when there has
been a processing failure, such as detecting an unknown key or
unknown signer.

Add a comment to secured messages. When enabled, the text you enter here
is always included in messages you encrypt or sign. Comments entered in
this field appear below the --BEGIN PGP MESSAGE BLOCK-- text header and
PGP Desktop version number of each secured message. These comments are
not visible in decrypted email.

Note: If you are using PGP Desktop in a PGP Universal Server-managed
environment, there may already be text in this field.
•

Protect sent message copies for IMAP accounts. This option is available for
standalone installations only. Select this checkbox if you want to protect
email messages as they are being copied to your IMAP Sent Items folder.
This option provides additional security so you can protect sensitive emails
that you have sent using your IMAP account.
When you select this option, then select how you want to secure the sent
message copies:

•

Encrypt Only (recommended). This option is the default. Select this
option to encrypt messages as they are copied to your Sent Items
folder.

•

Encrypt and Sign. Select this option to encrypt and sign messages as
they are copied to your Sent Items folder.

•

Sign Only. Select this option to sign (and not encrypt) messages as they
are copied to your Sent Items folder.

If the name of the folder is not a name that PGP Desktop recognizes (for
example, instead of "Sent Items" the folder is named "Outgoing Messages"), a
message is displayed asking you confirm if the name of the folder is where
your sent messages are typically stored. Note that the first message copied to
this folder is not encrypted and/or signed, but that subsequent messages
copied to this folder are.
•

Encrypt AOL® Instant Messages (AIM®). Enable if you want PGP Desktop to
encrypt instant message sessions with compatible instant messaging clients. The
other participant in the IM session must also be using PGP Desktop.
AOL® Instant Messenger™ and iChat software applications are compatible.
•

Display “PGP Enabled” in my AIM user information. When selected, PGP
Enabled is added to your screen name in such places as the AIM Buddy List
and the Get Buddy Info command. When disabled, your screen name is
displayed without PGP Enabled. The appearance of this text may vary
depending on your instant messaging client.

171

172

Setting Preferences
Messaging Preferences

•

Display the PGP lock icon over my buddy icon. When selected, the PGP
stylized lock icon is displayed with your buddy icon, so others can see that
the IM session is protected. When disabled, your icon is displayed normally.

Click Proxy Options to access advanced messaging settings.

Proxy Options
Click Proxy Options for advanced email and IM preferences.

Email Preferences
If your computer needs to have a proxy manually configured so that you can send and
receive email, you would use this feature.
PGP Desktop works between your email application and the mail server that provides
your mail. This configuration enables PGP Desktop to filter, or proxy, your email traffic
for you automatically. PGP Desktop can protect your messages, based on the applicable
policy, without interrupting your work.

Normally, you do not need to change the PGP Proxy settings. However, some users must
specify proxy settings manually. Choose the setting that your network administrator
recommends:
•

Automatic: The default, recommended setting. Your email is protected
automatically and transparently. Symantec Corporation recommends that you
leave this option selected unless you are instructed to use the manual proxy
setting.

•

Manual Proxy. This option is needed if your computer is “tunneling” through SSH
to your mail server, or if the computer on which you are running PGP Desktop also
functions as a mail server.
Note: If you are using a manual proxy and have multiple messaging services,
ensure that the redirect ports used by the messaging service are unique. By
default, PGP Desktop uses 10143, 10110, and 10025 for all messaging services.To
change the redirect ports for a messaging service, view the service and click
Settings. Change the protocol to IMAP and then change the Redirect local port.

Setting Preferences
Disk Preferences

Instant Messaging Preferences
If your computer is behind a network firewall, you may need to change the network port
that AIM uses for your IM chat sessions. Most users do not need to change this setting.

•

Override destination port. Select this checkbox to change the port that AIM uses
for your IM sessions. Change the value to one other than the default (5190). Your
network administrator can tell you if you need to change this setting and, if so,
what port number to use.

Disk Preferences
The Disk Preferences panel contains settings that apply to volumes protected using the
PGP Virtual Disk and the PGP Shredder features.

Note: If you are using PGP Desktop in a PGP Universal Server-managed
environment, these preferences may already be configured.
The Disk preferences are:

173

174

Setting Preferences
Notifications Preferences

•

Allow PGP Disks to unmount even while files are open. Normally, you cannot
automatically unmount a PGP Virtual Disk if any of the files in that volume are
open. Enabling this option allows unmounting even with open files, a practice
known as a forcible unmount.
Warning: You may lose data if you forcibly unmount a PGP Virtual Disk volume
with open files.

•

Unmount when computer goes to sleep. When enabled, PGP Desktop
automatically unmounts any mounted PGP Virtual Disk volumes when your
computer goes into Sleep mode.
•

•

Prevent sleep if disk(s) cannot be unmounted. This setting is inactive until
you select the Unmount when computer goes to sleep checkbox. This setting
prevents your computer from sleeping if a PGP Virtual Disk volume cannot
be unmounted.

Number of passes. The PGP Shredder feature removes your file(s) securely by
deleting them normally, then using numerous “0” characters to overwrite the disk
space that had been occupied by the files you just deleted.
Using this method, your files can be deleted very securely with only a few
overwriting “passes.” For this reason, a setting of 3 is the default, and offers an
extremely high level of security, but you can adjust this setting to reflect the level
of security that you desire (up to a maximum of 49 passes).
Be aware that the cost of added security is increased time needed to shred your
file(s), depending on several factors, particularly the speed of your computer’s
processor.
The recommended guidelines for number of passes are:

•

3 passes for personal use.

•

10 passes for commercial use.

•

18 passes for military use.

•

26 passes for maximum security.

Always warn me before shredding. Select this checkbox if you would like a
confirmation dialog box to appear before any shredding takes place. This gives you
a chance to double-check that only the files you intended are the ones that are to
be shredded. This option is selected by default.

Notifications Preferences
The Notifications Preferences panel contains settings that apply to the PGP Desktop
Notifier feature, which displays status messages in a corner of your screen when you
send or receive email messages. It also displays status messages when you use PGP
Desktop disk features.

Setting Preferences
Notifications Preferences

In a PGP Universal Server-managed environment, your administrator may have
specified certain notifications settings (for example, whether notifications are to be
displayed or the location of the notifier). In this case, the Notifications Preferences
panel is not available and not displayed.

The Notifications preferences are:
•

Use PGP Notifier: PGP Desktop Notifications can appear at any of the four corners
of your screen. Select a button to indicate the corner that you would like PGP
Desktop Notifications to appear. Click Preview to see how the PGP Desktop
Notification alert box looks in the specified corner.

•

Notify when processing outbound email: Select this checkbox if you want PGP
Desktop Notifiers to appear, informing you of encryption and/or signing status
when you send mail. Deselect this checkbox to stop PGP Desktop Notifications
from appearing when you send mail.

•

Ask me before sending email when the recipient’s key is not found: PGP Desktop
looks for a public key for every recipient of the email messages that you send. By
default, if it cannot find a public key for a recipient, it sends that email in the clear
(without encryption). If you select this PGP Desktop Notification option, you are
notified that this is the case, and given a chance to block the email so that it is not
sent.
For more information on the PGP Desktop default policy settings, see Services and
Policies (on page 79).

•

Always ask me before sending email: You can select this checkbox if you would
prefer approving every email that you send. You can review the encryption status
in the PGP Desktop Notification, and either send or block the email.

175

176

Setting Preferences
Advanced Preferences

•

Delay outbound email for n second(s) to confirm (where n is a number from 1-30;
the default is 4 seconds). If you would like a PGP Desktop Notification for every
message that you send—but you would prefer that they did not wait for your
explicit approval—you can select this option. Outbound email is delayed, and a PGP
Desktop Notifier displays, for the time period that you choose. If you want the
email to be sent, do nothing: the email is sent once the time interval elapses. If you
would like a closer look at the PGP Desktop Notification, move your cursor over it.
The PGP Desktop Notification changes from translucent to opaque in appearance,
and the outbound email is delayed while you review the PGP Desktop Notification
information. You can then allow the email to be sent, or block it.

•

Display notifications for incoming mail: For incoming email, you can choose the
extent to which you are notified of its status upon arrival. Your choices are:

•

When receiving secured email—A PGP Desktop Notification box is displayed
whenever you receive secured email. The box displays who the email is from,
its subject, its encryption and verification status, and the email address of
the person sending it.

•

Only when message verification fails—For incoming email, you see a PGP
Desktop Notification box only when PGP Desktop is unable to verify the
signature of the incoming email.

•

Never—If you do not need or want to see a PGP Desktop Notification box as
you receive email, select this option. This option does not affect PGP Desktop
Notifications for outgoing mail.

Notify for status of PGP Encrypted IM sessions: Select this checkbox if you would
like a PGP Desktop Notifier box to appear briefly when you begin a secure instant
message chat, and appear briefly again when the chat ends.

Advanced Preferences
The Advanced Preferences panel provides settings that most users will not need to
change.

The Advanced preferences are:

Setting Preferences
Advanced Preferences

•

Activate FIPS 140-2 Operational and Integrity Checks. Select this option if you or
your organization require FIPS 140-2 checks, but be aware that it slows down your
computer’s performance. You must reboot your computer for this setting to take
effect. This option is available only in standalone installations.

•

Use an HTTPS proxy to communicate with PGP Universal. Do not change these
settings unless you are instructed to by your network administrator.

If your PGP Universal Server installation requires a secure client/server connection via
a proxy, you can use these option settings to specify that. Your administrator can
supply you with the server name, the correct communications port, your user ID, and
your password, so you can configure this section correctly.

177

Working with Passwords and
Passphrases
Passwords and passphrases are used to protect things. In general, passphrases are
longer and use a wider variety of characters than do passwords.
For example, a simple password might be four-letter two words concatenated:
“whenjobs” without the quotes. A stronger password could use uppercase characters as
well: WhenJobs. A stronger yet password could add numbers: When9Jobs4.
Passphrases, in comparison, are longer and use a wider variety of characters. For
example, a simple passphrase might be: “Mb&1a>ttA.” without the quotes, but
including the period. This passphrase might seem difficult to remember easily, but in
fact it’s based on a simple phrase that is much easier to remember.
Passphrases can also be simple phrases, perhaps from a familiar book, that include the
punctuation and capitalization: “Because that’s not golf, I replied” including the quotes.
Although this may not seem like a strong passphrase, it is in fact at least twice as strong
as any of the other examples.
This section describes the differences between passwords and passphrases, tells you
about the Passphrase Quality Bar in PGP Desktop, and provides some guidelines for
creating strong passphrases.

In This Chapter
Choosing whether to use a password or passphrase..............................................179
The Passphrase Quality Bar.......................................................................................180
Creating Strong Passphrases.....................................................................................181
What if You Forget Your Passphrase?......................................................................182
Saving Your Passphrase in the Keychain ................................................................182

Choosing whether to use a password or passphrase
So how do you know whether to choose a password or a passphrase? It depends on what
you are trying to protect. The more valuable the information you are protecting, the
stronger the protection should be.
Most Word documents are not protected at all; the content is not valuable enough to
justify the effort. When you access your bank account online, some banks require only a
four-letter PIN; depending on the amount of money in that account, this very well may
be very poor security. You may use a free Hotmail email account for unimportant
correspondence; a simple password is adequate security. With your corporate email
account you send and receive proprietary product, customer, or financial information.
With PGP Desktop, for example, you create passphrases for both your PGP keypair and
for your PGP Virtual Disk volumes. If you create a weak passphrase for your PGP
keypair, and an attacker managed to get physical control of your private key file, all
they would need to do to be able to read your messages and send messages that appear
to be coming from you would be to figure out that passphrase.

180

Working with Passwords and Passphrases
The Passphrase Quality Bar

The Passphrase Quality Bar
When you create passphrases in PGP Desktop, the Passphrase Quality bar provides a
basic guideline for the strength of the passphrase you are creating. Nevertheless, it is a
much better guideline than just number of characters.
In general, the longer the bar, the stronger the passphrase. But what does the length of
the Passphrase Quality bar actually mean?
The Passphrase Quality bar compares the amount of randomness (entropy) in the
passphrase you enter against a true 128-bit random string (the same amount of entropy
in an AES128 key). This is called 128 bits of entropy.
(Entropy is a measure of the difficulty in determining a password or key.)
So if the passphrase you create fills up approximately half the Passphrase Quality bar,
then that passphrase has approximately 64 bits of entropy. And if your passphrase fills
the Passphrase Quality bar, then that passphrase has approximately 128 bits of
entropy.
So how strong is 128 bits of entropy? In the late 1990s, specialized “DES cracker”
computers were built that could recover a DES key in a few hours by trying all possible
key values.
Assuming you could build a computer that could recover a DES key in one second (the
computer would have to be able to try 255 keys per second), then it would take that
computer approximately 149 trillion (thousand billion) years to crack one 128-bit AES
key. In comparison, the universe is believed to be less than 20 billion years old.
How is the entropy of a particular character measured? The answer is, the bigger the
pool of characters there is to choose from when picking a particular character, the more
entropy is assigned to the chosen character.
For example, if you are told to choose a numeric PIN, you are restricted to the numbers
zero through nine; a total of 10 characters. This is a rather small pool, so the entropy
for a chosen character is relatively low.
When you are choosing a passphrase using the English version of PGP Desktop,
however, things are different. You have three pools of characters to choose from:
uppercase and lowercase letters (52 characters), numbers zero through nine (10
characters), and the punctuation characters on a standard keyboard (32 characters).
When you enter a character, PGP Desktop determines the entropy value for that
character based on the pool it is in and applies that value to the Passphrase Quality bar.
The same concept applies to the character sets of other languages; the larger the pool,
the more entropy per character. So if you were using an Asian or Arabic character set,
for example, some of which have hundreds of characters in the set, the amount of
entropy for a selected character would be correspondingly higher, and thus fill up the
Passphrase Quality bar that much faster.

Working with Passwords and Passphrases
Creating Strong Passphrases

Creating Strong Passphrases
Creating a good passphrase is a trade-off between ease of use and strength of the
passphrase. Longer passphrases, with a mixture of uppercase and lowercase letters,
numbers, and punctuation characters, are stronger, but they are also harder to
remember.
Studies have shown that passphrases that are harder to remember are more frequently
written down, which defeats the purpose of having a strong passphrase. It’s better to
have a somewhat shorter strong passphrase that you will remember than a longer
strong passphrase that you will write down or forget.
One common system for generating strong passphrases takes a phrase and reduces it to
individual characters. For example, the phrase:
My brother and I are greater together than apart.
becomes the passphrase:
Mb&1a>ttA.
This passphrase has 10 characters, and is a mix of uppercase and lowercase letters,
numbers, and punctuation characters. At 10 characters, this is a relatively short
passphrase. If you think 10 characters is not enough, consider either creating another
passphrase using the same method and then use both together or simply use a longer
phrase to start with.
Another approach is to use simple phrases that include punctuation and capitalization.
For example:
Edited by John Doe (not John Doe, Editor)
While not overly long or complicated, this is a strong passphrase. If you decide to use a
phrase from a familiar book, make sure not to lose the book.
When creating a passphrase in PGP Desktop, you can use up to 255 characters,
including spaces.
Another approach is to concatenate many short, common words. A method called
Diceware™ uses dice to select words at random from a special list called the Diceware
Word List, which contains 7776 short English words, abbreviations, and
easy-to-remember character strings. If you put together enough of these, you can create
a strong passphrase. The Diceware FAQ states you may achieve 128 bits of entropy
using a 10-word Diceware passphrase.
For more information about Diceware, see the Diceware Passphrase Home Page
(http://world.std.com/~reinhold/diceware.html).
When it comes to creating passphrases, here are some things you should do:
•

Use a phrase that is in your long-term memory. You are less likely to forget it that
way.

•

Make your passphrase at least eight characters long. Length is not the best
indicator of strength, but it’s still better than shorter.

•

Use a mixture of uppercase and lowercase letters, numbers, and punctuation
characters.

181

182

Working with Passwords and Passphrases
What if You Forget Your Passphrase?

Caution: Try to use only ASCII characters, if possible. This is particularly
important when using international keyboards, as some special characters are
not supported (for example, “§”) in passphrases.
•

Change your passphrase on a regular basis; every three months is a good rule of
thumb. The longer you use the same passphrase, the more time there is for
someone to figure it out.

Here are some things you should not do when creating passphrases:
•

Do not write down your passphrase.

•

Do not give your passphrase to anyone.

•

Do not let anyone see you entering your passphrase.

•

Do not use “password” or “passphrase.”

•

Do not use patterns. Not “abcdefgh” or “12345678” or “qwertyui” or “88888888”
or “AAAAAAAA.”

•

Do not use common words. Almost any skilled attacker is using a
password-cracking dictionary that tries regular words. Don’t put two common
words together, don’t use the plural of a common word, don’t use a common word
with the first letter capitalized.

•

Do not use numbers that pertain to you. If anyone knows these numbers, then an
attacker could find out. Don’t use your birthday, your phone number, your social
security number, or your street address.

•

Do not use names. Not the names of people, not the names of fictional characters,
not your pet’s name. Not where you vacationed last winter, not your login name,
not your company’s name. Not your favorite team’s name, not a body part, not a
name from any book, especially the Bible.

•

Do not use any of the above backwards, or with a preceding or following single
digit.

What if You Forget Your Passphrase?
If you forget your passphrase, you will never again be able to decrypt any information
encrypted to your key. You can, however, reconstruct your key if your PGP
administrator has implemented a key restoration policy for your company. For more
information, see PGP Key Reconstruction (see "Reconstructing Keys with PGP Universal
Server" on page 70, "If You Lost Your Key or Passphrase" on page 69) and contact your
PGP administrator.

Saving Your Passphrase in the Keychain
If desired, you can cache your key passphrases using the Mac OS X Keychain. When you
are prompted to enter a passphrase, select the box to Save passphrase in Keychain.
You can then access all PGP Desktop features without needing to enter your passphrase
each time.

Working with Passwords and Passphrases
Saving Your Passphrase in the Keychain

Subkeys are also saved in the Mac OS X keychain, so actions by subkeys are automatic
once the keychain has been unlocked.

183

Using PGP Desktop with PGP Universal
Server
PGP Universal Server allows enterprises to automatically and transparently (to end
users) protect email messages based on configurable policies the PGP administrator
establishes to enforce the organization’s security policies. PGP Universal also lets PGP
administrators manage PGP Desktop deployments to users in their organization. For
more information about the PGP Universal Server, see PGP Universal Server on the PGP
website (http://www.pgp.com/products/universal/index.html).
Using PGP Desktop in a PGP Universal Server-managed environment gives you proven
PGP encryption technology all the way to your desktop, plus the other security features
in PGP Desktop: PGP Whole Disk Encryption, PGP Virtual Disk volumes, PGP Zip
archives, and PGP Shred, among others.
To use PGP Desktop in a PGP Universal Server-managed environment, you must install
PGP Desktop using an installer application you receive from your PGP administrator.
If you are using a version of PGP Desktop you purchased for home use, and are not
using it in a corporate environment, you are likely using a standalone version, and this
section does not apply to you.
Caution: If you are using PGP Desktop in a corporate environment and you obtained
your PGP Desktop installer from a different source other than your PGP
administrator, you should check with your PGP administrator before installing or
using that version of PGP Desktop.
This section describes how using PGP Desktop is different in a PGP Universal
Server-managed email domain.

In This Chapter
Overview .......................................................................................................................185
For PGP Administrators .............................................................................................186
Manually binding to a PGP Universal Server..........................................................187

Overview
Your PGP Desktop installer will have been configured by your PGP administrator in one
of the following ways:
•

No policy settings. Your copy of PGP Desktop will not have any built-in settings;
you can use any feature your license supports.

•

Auto-detect policy settings. Your copy of PGP Desktop will contact the PGP
Universal Server that created the installer and download the appropriate settings.
The settings it receives may require you to use PGP Desktop features in specific
ways.

186

Using PGP Desktop with PGP Universal Server
For PGP Administrators

•

Preset policy settings. Your copy of PGP Desktop will have the appropriate
settings built in. These settings may require you to use PGP Desktop features in
specific ways.

The result of your copy of PGP Desktop receiving settings from a PGP Universal Server
means you may have to use PGP Desktop features in specific ways. This includes:
•

You may have to take certain actions when you install PGP Desktop: you may have
to whole disk encrypt your boot drive or create a PGP Virtual Disk volume, for
example.

•

You may be allowed or required to use PGP Desktop features in certain ways: you
may be required to encrypt your AIM instant messaging sessions or you may be
allowed to automatically shred files when deleting them, for example.

•

You may be prevented from using certain PGP Desktop features: you may be
prevented from using conventional encryption and creating self-decrypting
archives (SDAs), for example.

•

You may be required to use to certain messaging policies: you may have to encrypt
and sign messages to certain email domains, for example.

•

You may have certain features disabled, such as PGP Messaging or PGP NetShare
(on Windows systems), or you may have a customized PGP Whole Disk Encryption
BootGuard screen (on Windows systems). For more information, see Features
Customized by Your PGP Universal Server Administrator (on page 3).

Those features of PGP Desktop that can be managed by a PGP administrator in a PGP
Universal Server-managed environment are noted in their descriptions throughout this
User’s Guide.
Contact your PGP administrator for more information about the differences when using
PGP Desktop in a PGP Universal Server-managed environment.

For PGP Administrators
If you are a PGP administrator managing the rollout of PGP Desktop to some or all
users in your organization, Symantec Corporation recommends you allow your PGP
Desktop users to manage their own keys, called Client Key Mode.
When you are preparing to create the PGP Desktop installers on your PGP Universal
Server, you can control whether your PGP Desktop users are able to manage their own
keys, Client Key Mode, or whether the PGP Universal Server will manage their keys,
called Server Key Mode.
These settings are established in the Key Management section of the Key Setup: Default
screen, which is part of the configuration of the default user group policy for internal
users (User Group > Policy Options > Key Setup: Default in the PGP Universal Server’s
administrative interface).
For PGP Desktop users, Client Key Mode is the better choice because:
•

Many PGP Desktop features require the user to have control of their private key. If
the PGP Universal Server is managing that private key, those features will be
unavailable to your PGP Desktop users.

•

If you specify Server Key Mode, certain options you pre-configure for your PGP
Desktop users will not be available. For example, the automatic creation of PGP
Virtual Disks is not possible.

Using PGP Desktop with PGP Universal Server
Manually binding to a PGP Universal Server

Manually binding to a PGP Universal Server
If you manually bind to a PGP Universal Server using PGP Desktop (when viewing a
Messaging Service, click Server Settings) and enroll, you will download only the email
policy and not the consumer policy. Your PGP Universal Server administrator may have
specified other options in the consumer policy (such as key modes, forcing the
encryption of disks, and so on). To be fully managed and enforce consumer policy you
need to use a PGP Universal Server "stamped" installation. Contact your administrator
to obtain a stamped installation if you do not have one.
In addition, when you manually bind to a PGP Universal Server, the file
PGPtrustedcerts.asc does not exist in C:\Documents and
Settings\AllUsers\Application Data\PGPCorporation\PGP. If you want to manually bind
to a PGP Universal Server, you will need to create this file and ensure that the user ID of
the organization key in that file matches the server specified by the PGPSTAMP (the
domain name and IP address must match).

187

Index
.
.Mac, syncihronizing keys with • 167

A
Additional Decryption Keys (ADKs) • 64
AES, algorithm in PGP Virtual Disk • 149
alternate passphrases • 127, 144
authentication in PGP Whole Disk Encryption
method used, determining • 121
Automatic mode • 172

B
basic steps for using • 12
binding, manually to a PGP Universal Server • 187
biometric word list • 51
boot disks, encrypting • 117, 118, 135
BootGuard • See PGP BootGuard screen

C
CAST, algorithm in PGP Virtual Disk • 149
changing
a key's passphrase • 55
your passphrase • 55
changing your passphrase • 54
characters, supported • 122
characters, supported in PGP WDE • 122
Clear Verification History • 159
Client Key Mode (CKM) • 101
compacting, PGP Virtual Disk • 143
conventional encryption • 31
creating • 40, 181
a messaging policy • 86
a messaging service • 81
a new PGP Virtual Disk volume • 138
passphrases, strong • 181

D
decrypt and verify
in Finder • 33
decrypting • 133
default policies • 79, 92, 93, 94
deleting
digital signatures • 55
keys • 55
keys from your keyring • 55
subkeys • 64
user IDs • 55
designated revoker • 66
digital signature deleting • 55
digital signatures • 44, 46, 55, 62, 73
disabling public keys • 56

disk read/write error • 121
disks
adding users to encrypted • 127
encrypting • 121, 122
errors during encryption • 124
removable • 133
supported in PGP WDE • 119
using encrypted • 125
distributing virtual disks • 149
dock icon • See PGP Dock icon

E
email • 75
copying public keys from • 48
copying to your inbox • 111
exporting
key to a file • 46
exporting messages to your inbox • 111
including your public key in • 45
key modes • 101
multiple accounts • 84
notifiers • 27
opening in PGP Viewer • 110
securing • 75
services and policies • 79
email options • 172
enabling public keys • 56
encrypt • 118, 121
in Finder • 31
encrypt and sign
in Finder • 31
encrypting IM sessions • 75, 105, See PGP
Messaging
encryption
adding users to • 127
algorithm used • 149
calculate duration of in PGP WDE • 120
deleting users from PGP WDE • 128
disk errors during • 124
disks or partitions • 122
pilot test • 121
re-encrypting disk or partition • 128
using PGP WDE-encrypted disk • 130
encryption disk read/write error • 121
encryption options
conventional • 31
MacBinary • 31
Shred original • 31
text output • 31
Entourage 2004, integrating with • 20
evaluation licenses • 3
exchanging virtual disks • 149
extract PGP Zip archives in Finder • 35

19
0

Index

F
files
exporting public keys to • 46
importing public keys from • 52
Finder, accessing from • 27, 31
fingerprint, verifying digital • 56
flags, specifying usage on subkeys • 63
forensics, recovering data • 131
forgotten passphrases • 70
Free Space Wipe • See shredding free space

G
General preferences • 166
granting trust • 59
granting trust for key validations • 59
Guarded Key Mode (GKM) • 101

H
hibernation • See sleep, Mac OS X and PGP WDE

I
importing
a PGP key in Finder • 34
public keys, from files • 52
incoming email • 76
installing • 21
installing PGP Desktop • 15
instant messaging • 105
options • 173

K
key modes • 101
key reconstruction • 19, 70, See reconstructing your
key
key size
setting • 62
trade-offs • 62
keyboard, supported in PGP WDE • 119
keyboards, supported • 119
keychain, saving passphrase in • 182
keypair • 10
keyrings • 43, 55
keys • 37, 51

changing passphrase • 55
deleting from your keyring • 55
disabling • 56
distributing, public • 44
email addresses, adding to • 53
email, including in • 45
enabling • 56
exporting • 46
Finder, adding in • 35
granting trust for validations • 59
keyserver, uploading to • 45
lost • 69, 70
multiple user names and email addresses • 53
names, adding to • 53
preferences • 167
protecting • 73
reconstructing • 70
rejoining a split key • 67, 68
replacing a photo ID • 52
revoking • 66
saving public to file • 46
setting size of • 62
signing • 57
splitting • 67
subkeys • 60
synchronizing, Keys Preferences • 167
verifying public • 56
keyserver
getting someone's public key from • 47
searching • 47
sending your public key to • 44
using to circulate revoke keys • 66
keyservers • 10
getting someone's public key from • 47
searching • 47
sending your public key to • 44

L
licensing • 3, 4, 19, 117
local policy • See offline policy
log, messaging • 103
logging in, PGP BootGuard screen • 125
lost key or passphrase • 69

M
mail servers, see messaging services • See
messaging
mailing list policies • 92, 93, 94
managed users • 2
Menu Bar icon • 25
messaging • 79
multiple • 84
notifiers • 27
troubleshooting • 85
Messaging Log • 103

Index

Messaging preferences • 170
mounting PGP Virtual Disk volumes • 142
moving PGP Desktop to another computer • 21
multiple messaging services • 84

N
NetShare • See PGP NetShare
Notifier feature
described • 27
for incoming messages • 28
for instant messaging • 29
for outgoing messages • 28

O
offline policy • 29, 78, 80
options • See preferences
outgoing email • 78
overview, of PGP Desktop • 1

P
partitions, encrypting • 127
passphrase
adding alternate for PGP Virtual Disk • 127
changing • 55
changing on a key • 55
forgotten • 182
saving in keychain • 182
passphrase quality bar • 180
Passphrase Quality bar • 180
passphrases • 150, 179
changing • 54, 128, 155
forgotten • 69, 70
strong, creating • 181
supported characters in PGP WDE • 122
password • 121, 122
passwords • See passphrases
perpetual licenses • 3
PGP administrator • 130, 185
PGP BootGuard screen • 122, 125
PGP Desktop

accessing via Finder • 27
described • 9
icon in Menu Bar • 25
in PGP Universal-managed environment • 185
installation • 16
installing • 16
main screen • 23, 24
Notifier feature • 27
PGP tray icon • 25
policies described • 79
Setup Assistant • 19
SSL/TLS support • 100
system requirements • 15
uninstalling • 20
upgrading • 17
PGP Disk
preferences • 173
PGP Dock icon • 26
PGP Global Directory • 9
PGP Keys • See keys
add to keyring in Finder • 35
creating a keypair • 40
expert mode key settings • 41
import in Finder • 34
viewing • 38
PGP Keyservers List • See keyservers
PGP Log • 103
PGP Messaging • 9, 75
creating a policy • 86
creating a service • 81
log • 103
services and policies • 79
services described • 79
PGP NetShare • 9
PGP Shred • 9, 161
described • 161
PGP Universal • 3, 70, 185
PGP Universal Server • 9, 70, 130, 185, 186, 187
PGP Universal Services Protocol (USP) • 48
PGP Viewer • 109, 110, 111, 112
email messages • 110, 111
overview of • 109
PGP Virtual Disk • 9, 137, 150

19
1

19
2

Index

alternate users • 144
backing up • 148
creating • 138
creating a new volume • 138
deleting • 147
encryption algorithms • 149
exchanging • 149
maintaining • 148
mount in Finder • 34
mounting • 142
properties • 141
re-encrypting • 143
security precautions • 150
unmounting • 141
volume mount in Finder • 34
PGP Whole Disk Encryption • 9
adding users • 127
authentication options • 121
automatic backup software • 129
backing up encrypted disks • 129
changing a passphrase • 128
decrypting a disk • 133
decrypting an encrypted disk • 133
deleting users • 128
disk read/write error • 121
disk types, supported • 119
disk, maintaining security of • 126
disk, using encrypted • 125
encrypting a disk • 118, 121
encryption duration, calculating • 120
licensing • 117
PGP Universal Server, managed • 130
prepare disk for • 118
preparing to encrypt • 118
recovery disc • 132
recovery tokens • 130
re-encrypting • 128
re-encrypting an encrypted disk • 128
removable drives • 133
security precautions • 134
supported disk types • 119
uninstalling • 129
users, working with • 127, 128
viewing key information • 127
PGP Zip • 9, 157
PGP Zip archives
Clear Verification History • 159
creating • 158
described • 157
extract in Finder • 35
opening • 159
verify signed • 159
photo ID • 52

adding • 52
removing • 52
removing from a key • 52
policies • 79
creating • 86
creating messaging • 86
default policies • See default policies
deleting • 99
editing • 95
examples • 86
examples of messaging • 92
viewing • 80
preferences • 112, 165
General • 166
instant messaging • 173
Keys • 167
Messaging • 170
PGP Disk • 173
PGP Viewer • 112
primary name, on key • 53
private keys • 10, 42
protecting keys • 73
public keys • 10
advantages of sending to key server • 44
copying from email messages • 48
distributing to others • 44
email message, including in • 45
enabling and disabling • 56
exporting to files • 46
getting from a keyserver • 47
getting others • 46
importing from files • 52
saving to file • 46
searching keyserver • 47
sending to keyserver • 44
signing • 57
trust • 59
verifying • 56, 57

R
read/write error • 121
reconstructing keys • 70
reconstructing your key • 44, 70
recovering data from an encrypted drive • 131
recovery tokens • 130
re-encrypting • 128
re-encrypting a disk • 128, 143
rejoining split keys • 67, 68
removable disks • 133, 134
removable drives in PGP WDE • 133
removing
a photo ID from a key • 52
subkeys • 64
resetting key mode • 101
revokers, key • 66
revoking

Index

keys • 66
signature, from a key • 58
subkeys • 64

S
S/MIME email, importing certificates in • 54
searching keyserver • 47
secure instant messaging (IM) • 105
security precautions • 134, 150
separate signing subkey • 9
Server Client Key Mode (SCKM) • 101
Server Key Mode (SKM) • 101
services • 79
creating • 81
deleting • 83
disabling • 83
enabling • 83
viewing • 80
Services menu
PGP functionality • 31
services, messaging • 79, 84
shredding
described • 161
in Finder • 33
shredding free space • 9
signatures, deleting from keys • 55
signing • 55
in Finder • 31
keys • 55, 57
public keys • 57
sleep, Mac OS X and PGP WDE • 135
smart card • 10
splitting keys • 67
SSL/TLS support • 100
strong passphrases • 181
subkey usage • 63
subkeys • 60
creating new • 62
expiration • 60, 62
icons • 60
looking at • 62
properties • 60
removing • 64
revoking • 64
separate • 60
setting size of • 62
size • 60
symbols • 60
validity • 60
viewing • 60
working with • 60
subscription licenses • 3
support, contacting • 6
system partition, modifying • 127
system requirements • 15

T
technical support • 6
terminology • 2, 9, 11, 79, 101
text output • 31
troubleshooting • 85
trust
granting for key validations • 59
public keys • 59
trust, granting for key validations • 59
Twofish, algorithm in PGP Virtual Disk • 149

U
uninstalling • 20, 129
unmanaged users • 2
unmounting • 155
PGP Portable Disks • 155
PGP Virtual Disk volumes • 141
Unversal Server • See PGP Universal
update policy • 78
upgrading • 19
usage flags, on subkeys • 63
usage flags, specifying • 63
user names, on keys • 53
users • 144
PGP Whole Disk Encryption, adding or deleting
from • 127, 128
USP • See PGP Universal Services Protocol (USP)

V
validating keys • 59
granting trust for • 59
validity • 51
verifying
a public key • 57
PGP Zip signed archives • 159
viewing subkeys • 60
virtual disks • See PGP Virtual Disk

W
wildcards, in policies • 91
wiping files • See shredding free space
word list, biometric • 51

X
X.509 certificates • 54
X.509 certificates, adding to keypair • 55

19
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