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PGP Desktop for Mac OS X
Quick Start Guide
Version 10.2

• Using PGP Viewer (page 5)

What is PGP Desktop?

• Using PGP WDE to Encrypt a Drive (page 6)

PGP Desktop provides comprehensive security for desktops
and laptops, making it possible for enterprises, workgroups,
and individuals to protect sensitive information without
changing the existing IT infrastructure or disrupting work
processes. This award winning, easy-to-use solution encrypts
email, files, virtual volumes, and entire disks from a single
desktop application.

• Creating PGP Virtual Disk Volumes (page 8)
• Creating a PGP Zip Archive (page 9)
• Using PGP Shred to Shred Files (page 10)
• Getting Assistance (page 11)

The PGP Desktop family of applications have been combined
into several bundles.

New to PGP Desktop?

ƒ

PGP Desktop Professional includes PGP Desktop Email
and PGP Whole Disk Encryption

ƒ

PGP Whole Disk Encryption includes PGP Whole Disk
Encryption

Use this step-by-step guide to get started. You will find that,
with PGP Desktop, protecting your data will be as easy as
turning a key in a lock.

PGP Desktop Email

ƒ

This Quick Start Guide helps you install PGP Desktop and
get started.

ƒ

The PGP Desktop User’s Guide provides more detailed
information on PGP Desktop. In it, you will learn what a
keypair is, why you might want to create one, how to
create one, and how to exchange keys with others so you
can encrypt your own data and share data securely with
others.

Use PGP Desktop Email to automatically and transparently
encrypt, sign, decrypt, and verify email message through
policies you defined for you by administrators, or policies you
control if you are not part of a PGP Universal Server-managed
environment.

Note: A PGP Desktop license provides you with access to
a certain set of PGP Desktop features. Certain other
features of PGP Desktop may require a different license.
For more information, see the Licensing section of the
PGP Desktop User’s Guide.

PGP Whole Disk Encryption
Use PGP Whole Disk Encryption (PGP WDE) to lock down the
entire contents of your system or an external or USB flash
drive you specify.
ƒ

In addition, use PGP Desktop to:
ƒ

Use part of your hard drive space as an encrypted virtual
disk volume with its own drive letter.

ƒ

Create protected Zip archives.

ƒ

Completely destroy files and folders so that nothing can
recover them.

For deployment, management, and policy enforcement
information for PGP Desktop, see the PGP Universal
Server Administrator’s Guide.

After installation, PGP Desktop prompts you to create a PGP
keypair. A keypair is the combination of a private key and a
public key.
ƒ

Keep your private key and its passphrase private, as the
name suggests. If someone gets your private key and its
passphrase, they can read your messages and
impersonate you to others. Your private key decrypts
incoming encrypted messages and signs outgoing
messages.

ƒ

Your public key you can give to everyone. It does not have
a passphrase. Your public key encrypts messages that
only your private key can decrypt and verifies your
signed messages.

Contents
• What is PGP Desktop? (page 1)
• New to PGP Desktop? (page 1)
• Understanding the Basics (page 1)
• What Am I Installing? (page 2)
• System Requirements (page 2)
• Installing PGP Desktop (page 2)

Your keyring holds both your keypairs and the public keys of
others, which you use to send encrypted messages to them.
Click the PGP Keys Control Box to see the keys on your
keyring:

• Starting PGP Desktop (page 3)
• The PGP Desktop Main Screen (page 3)
• Using PGP Desktop Email (page 3)

1

1

The icon for a PGP keypair has two keys, denoting the
private and the public key. Alice Cameron has a PGP
keypair in this illustration, for example.

2

The icons for the public keys of others have just one key.
Ming Pa’s public key, for example, has been added to the
keyring shown in this illustration.

contrast, immediately overwrites files multiple times. This is
so effective that even sophisticated disk recovery software
cannot recover these files. This feature also completely wipes
free space on your drives so your deleted data is truly
unrecoverable.
Key Management manages PGP keys, both your keypairs and
the public keys of others. You use your private key to decrypt
messages sent to you encrypted to your public key and to
secure your PGP Virtual Disk volumes. You use public keys to
encrypt messages to others or to add users to PGP Virtual
Disk volumes.

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

What Am I Installing?

ƒ

Apple Mac OS X10.5.x, 10.6.x, or 10.7.x (Intel)

ƒ

512 MB of RAM

PGP Desktop uses licensing to provide access to the features
you purchase. Depending on the license you have, some or all
of the PGP Desktop family of applications will be active.

ƒ

64 MB hard disk space

ƒ

PGP Desktop Email is a member of the PGP Desktop family of
applications. You can use PGP Desktop Email to automatically
and transparently encrypt, sign, decrypt, and verify email
messages through policies you control. You can also use PGP
Desktop Email to encrypt IM sessions for clients such as AIM
and iChat. Both users must have PGP Desktop Email enabled.

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 a member of the
PGP Desktop family of applications. You can use PGP WDE to
lock down the entire contents of your system or an external or
USB flash drive you specify. Boot sectors, system files, and
swap files are all encrypted. Whole disk encrypting your boot
drive means you do not have to worry if your computer is lost
or stolen: to access your data, an attacker would need the
appropriate passphrase.

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.

This document contains instructions for viewing the features
activated by your license.

PGP Virtual Disk volumes uses part of your hard drive space
as an encrypted virtual disk volume with its own drive letter.
A PGP Virtual Disk is the perfect place for storing your
sensitive files; it is as if you have stored them in a safe. When
the door of the safe is open (when the volume is mounted),
you can change files stored in it, take files out of it, and move
files into it. Otherwise (when the volume is unmounted), all
the data on the volume is protected.

Installing PGP Desktop
Symantec Corporation recommends exiting all open
applications before you begin the install. The installation
process may require a system restart.
Note: You must have administrative rights on your system in
order to install the update.

PGP Zip adds any combination of files and folders to an
encrypted, compressed, portable archive. PGP Desktop must
be installed on a system to create or open a PGP Zip archive.
PGP Zip is a tool for securely archiving your sensitive data,
whether you want to distribute it to others or back it up.

The PGP Desktop installer walks you through the installation
process.
To install PGP Desktop on your Mac OS X system

PGP Shredder completely destroys files and folders so that
even file recovery software cannot recover them. Deleting a
file using the Windows Recycle Bin (on Windows systems) or
Trash (on Mac OS X systems) does not actually delete it; it sits
on your drive and eventually gets overwritten. Until then, it is
trivial for an attacker to recover that file. PGP Shredder, in
2

1

Quit all other applications.

2

Mount the PGP DiskCopy image.

3

Double-click PGP.pkg.

4

Follow the on-screen instructions.

5

If prompted to do so, restart your system.

• Mount an existing PGP Virtual Disk.

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.

• Synchronize keys.
• Shred files.

4

PGP Desktop is managing for you.

5

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 disk or managing encrypting removable disks
using the PGP Whole Disk Encryption feature.

6

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.

Licensing
To see what features your license supports, open PGP Desktop
and select PGP > License. Click Details. The details of your
license are displayed.

7

Starting PGP Desktop
PGP Desktop Main Screen

ƒ

Using the PGP Desktop Icon in the Menu Bar

ƒ

Using the PGP Dock Icon

ƒ

Using the Mac OS X Finder

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

There are four main ways to access PGP Desktop:
ƒ

The Keys item. Gives you control over the PGP keys that

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

Using PGP Desktop Email
PGP Desktop Email automatically and transparently encrypts
and signs outgoing messages and decrypts and verifies
incoming messages. All you need to do is to send and receive
your email just as you always have; PGP Desktop Email will
take care of the rest.

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

Sending Encrypted Email
After installation, PGP Desktop Email inserts itself between
your email client and your mail server and watches your
email traffic.
When incoming messages arrive, PGP Desktop Email
intercepts them before they get to your inbox and
automatically attempts to decrypt and verify them; it uses
your private keys to decrypt and the public keys of others to
verify. When it is done with your messages, PGP Desktop
Email delivers them to your inbox.
In most cases, you do not have to do anything special;
decrypted incoming messages will appear in your inbox just
like any other incoming messages.

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.

2

The PGP Desktop Work area. Displays information

When you send outgoing messages, PGP Desktop Email
intercepts them on the way to your mail server and
automatically attempts to encrypt and sign them, based on
configured policies.
Again, you do not have to do anything special; just create your
messages using your email client and send them—PGP
Desktop Email handles everything else.

about and actions you can take for the selected item.

3

Details of how PGP Desktop Email transparently handles your
incoming and outgoing messaging is found in the following
sections.

The Toolbar. Provides access to frequently used features.
You can:
• Create a new PGP Zip archive.
• Create a new PGP Virtual Disk.

3

Incoming Messages

directory at PGP Global Directory (https://keyserver.pgp.com) ,
or ask them to send their public key to you directly by email.

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):
ƒ

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.

ƒ

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.

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.

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.

Default Policies
PGP Desktop Email includes four default policies:

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.
ƒ

ƒ

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.

ƒ

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

ƒ

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

ƒ

Require Encryption: [PGP] Confidential. 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 will not be sent. This policy
gives you a way to easily handle messages that must be
sent encrypted or not sent at all.

ƒ

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
be sent (unless you flag the message as Confidential),
albeit in the clear, even if a key to encrypt it to the
recipient cannot be found.

Creating New Policies

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.

PGP Desktop Email includes the ability to create and use new
policies in addition to the four default policies. You can create
policies based on a wide variety of criteria. If you are using
PGP Desktop Email in a PGP Universal Server-managed
environment, your messaging policies and other settings may
be controlled by your organization’s PGP administrator.

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

For complete information about how to create and implement
messaging policies, see the PGP Desktop User’s Guide.

4

Was My Message Encrypted?

and decrypt and verify incoming messages. When PGP
Desktop is doing this, it is called “in the mail stream.”

Because PGP Desktop Email does its work automatically and
transparently, from time to time you may find yourself
wondering, was my message really sent encrypted? The
answer is probably yes, but there are ways to make certain.

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

Opening an Encrypted Email Message or
File

Notifier Alerts

Use PGP Viewer to open (decrypt, verify, and display)
encrypted message files of the following types:

PGP Desktop Notifier alerts are a feature of PGP Desktop that
both tell you what is going on with your messaging and give
you control over it.
For example, when you send an encrypted message, the
Notifier alert appears in the lower right corner of your screen.
It shows:
ƒ

Subject.

ƒ

Who it is being sent to.

ƒ

Keys found for the recipient.

ƒ

Status of the message.

What PGP Desktop Email did to the message.

ƒ

Who signed the message.

.pgp: Created by a PGP application.

ƒ

.eml: Created by Outlook Express or Thunderbird.

ƒ

.emlx: Created by Apple's Mail.app program on Mac OS X
systems.

ƒ

.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

To view more information about the message being sent, click
More. Now you also see:
ƒ

ƒ

For more information about Notifiers, see the PGP Desktop
User’s Guide.

1

Open PGP Desktop and select the PGP Viewer tab.

2

Click Open File in PGP Viewer or select Viewer > Open
File in PGP Viewer.

3

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.

Note: 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.

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

The PGP Log lists a variety of actions that PGP Desktop is
taking to secure your messaging.

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.

5

For example, the message whose Notifiers are shown above
generated this entry in the PGP Log. It shows:

Click Smaller to make text smaller or Bigger to make text
larger.

6

Click Rich Text to display the message or file in RTF (rich
text format) or Plain Text for plaintext.

7

Click Print to print the message or file.

PGP Log

1

That an outgoing message was sent, who sent it, and what
the subject was.

2

The time it was encrypted, the email address it was
encrypted to, and the email address it was sent from.

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

Using PGP Viewer

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.

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
5

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.
2

1

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

2

Click Encrypt a Disk. The Encrypt Whole Disk screen is
displayed, showing a listing of disks on your system that
can be protected.

3

From the Select a disk list, select the disk you want to
protect.

4

In the Secure with section, specify how you want to
access your protected disk. Select Public Key user or
Passphrase user.

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.

3

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.

2

In the Export Message dialog box, specify the desired
filename, location, and format for the file, then click
Export.

Note: If you are encrypting a boot disk, you can only use
passphrase authentication, so PGP Desktop selects
Passphrase User for you and skips to the Add PGP
Whole Disk User screen.

PGP Viewer saves the file to the specified location.

Specifying Additional Options
Use the Tools button on the PGP Viewer Toolbar (on the far
right) to specify several PGP Viewer features:
ƒ

Text Encoding: Specify the text encoding format for the
message currently being displayed by PGP Viewer.

ƒ

Show Remote Images: Display external resources
(images, CSS style sheets, iframe content, and so on) for
the message currently being displayed by PGP Viewer.
You can specify that PGP Viewer automatically displays
external resources in Preferences.

ƒ

View Message Source: Display the source of the message
currently being displayed by PGP Viewer. Viewing the
message source can tell you more information about the
message.

ƒ

Preferences: Display the PGP Viewer Preferences dialog
box.

Using PGP WDE to Encrypt a Drive
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.

ƒ

To protect your disk with a public key, select Public
Key, then click Continue. The Add PGP Whole Disk
User screen is displayed. 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 is displayed with a
summary of how your disk will be encrypted. This
option is only available if you are encrypting a
removable disk.

ƒ

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.
Click Continue. The PGP Whole Disk Encryption
Summary screen is displayed with a summary of how
your disk is will be encrypted.

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 (in the PGP
Desktop for Mac OS X User's Guide).

Before you encrypt your disk, be sure to back it up so that you
won’t lose any data if your laptop or computer is lost, stolen,
or you are unable to decrypt the disk.
Backup software works normally with PGP WDE; any files the
software backs up will be decrypted before being backed up.
6

5

Review the information, then click Encrypt. The
encryption process begins and the Encryption Progress
screen is displayed.

6

Click Close. The PGP Desktop application window is
displayed and the encryption process continues in the
background. A bar shows how the encryption process is
progressing.

ƒ

Ensure the health of the disk before you encrypt it. If
PGP WDE 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 7).

ƒ

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.

ƒ

Consider the time it will take to encrypt the disk and
prepare accordingly. See Calculate the Encryption
Duration (on page 8).

ƒ

Run a pilot test to ensure software compatibility. As a
good security practice, Symantec Corporation
recommends testing PGP WDE on a small group of
computers to ensure that PGP WDE 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 WDE and
can cause serious disk problems, up to and including loss
of data. See Run a Pilot Test to Ensure Software
Compatibility (on page 8) for known interoperability
issues, and review the PGP Desktop Release Notes for the
latest updates to this list.

ƒ

Ensure that Sleep mode has been disabled. PGP Desktop
is not compatible with hibernation mode on Mac OS X
systems.

ƒ

Using Apple Boot Camp. 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.

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.
7

During the encryption process, you can do the following:
ƒ

To temporarily stop the encryption process, click
Stop. The Encryption is not complete dialog box is
displayed.

ƒ

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.

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.

PGP WDE Best Practices
Before you encrypt your disk, there are a few tasks you must
perform to ensure successful initial encryption of the disk.
ƒ

Determine whether your target disk is supported. See
"Supported Disk Types" in the PGP Desktop User’s Guide
for more details on what types of disks are supported.

ƒ

Make sure you use supported characters in your
passphrase. See "Supported Characters" in the PGP
Desktop User’s Guide for more details on what characters
are supported for passphrases.

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
7

encryption are logged to the management server and the
encryption process continues.

Run a Pilot Test to Ensure Software
Compatibility

Best Practices Recommendation

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.

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.

Creating PGP Virtual Disk Volumes

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.

The PGP Virtual Disk Volumes feature uses part of your hard
drive space as an encrypted virtual disk volume. You can
create additional users for a volume so that people you
authorize can also access the volume.
8

In PGP Desktop, select the PGP Disk item and then click
New PGP Virtual Disk.

9

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.

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:
ƒ

the size of the disk

ƒ

the processor speed and number of processors

ƒ

the number of system processes running on the computer

ƒ

the number of other applications running on the system

ƒ

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.

10 Specify the type of authentication you want to use for the
primary user of this PGP Virtual 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.

ƒ

To protect your PGP Virtual Disk with your keypair,
select Public Key.

ƒ

To protect your PGP Virtual Disk with a passphrase,
select Passphrase user.

11 To view or change the advanced options settings, select
the Advanced Options checkbox. The Cipher and Format
options are displayed.
Caution: The default Advanced Options settings are
appropriate for most users. Avoid changing these
settings if you are unfamiliar with them.
ƒ

8

From the Cipher menu, select the encryption
algorithm that you would like to use to protect your

PGP Virtual Disk: AES-256 (256 bits) or CAST5
(128-bits). For more information about these
encryption algorithms, see The PGP Virtual Disk
Encryption Algorithms in the PGP Desktop for Mac OS
X User's Guide.
ƒ

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.

From the Format menu, select the disk format that
you would like to use with your PGP Virtual Disk:
MS-DOS. Use if you intend to share this PGP Virtual
Disk with someone using PGP Desktop 10.2 for
Windows.

14 Select a file name and location for the PGP Virtual Disk,
then click Save.
15 Review the information on the PGP Disk Creation
Summary screen. When you are finished, click Create.

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+.

16 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.

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.)

17 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.

Mac OS Extended (Case-sensitive, Journaled). Use if
case-sensitive Journaling is enabled on your system.

Creating a PGP Zip Archive

Mac OS Standard. For backwards compatibility with
older Mac OS operating systems. The minimum size is
512 KB.

PGP Zip archives let you put any combination of files and
folders into a compressed, portable archive. There are three
kinds of PGP Zip archives:

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.

ƒ

Recipient keys. Encrypts the archive to public keys. Only
the holder of the corresponding private keys can open the
archive. This is the most secure kind of PGP Zip archive.
Recipients must be using PGP software (for Windows or
Mac OS X).

ƒ

Passphrase. Encrypts the archive to a passphrase, which
must be communicated to the recipients. Recipients must
be using PGP software (for Windows or Mac OS X).

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.

ƒ

Sign only. Signs the archive but does not encrypt it,
allowing you to prove you are the sender. Recipients must
be using PGP software (for Windows or Mac OS X) to open
and verify the archive.

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).

The Passphrase and Sign only PGP Zip types are described in
detail in the PGP Desktop User’s Guide; they are described
briefly here.

You can see the format of an existing Mac OS X drive
by selecting the drive, then selecting Get Info from
the File menu.
12 Click Continue.
13 The next step depends on whether you chose public key
or passphrase authentication:
ƒ

1

Enter the appropriate passphrase, then click OK. The
Save As dialog box is displayed. Continue with the
next step.
ƒ

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
9

Open PGP Desktop and select the PGP Zip item. The PGP
Zip dialog box is displayed.

2

Click Create new PGP Zip. The Untitled PGP Zip dialog
box is displayed.

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.
7

Select the type of encryption you want to use:
ƒ

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.

ƒ

3

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:
ƒ

Dragging and dropping the files/folders into the list.

ƒ

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.

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.
ƒ

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

5

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.

8

Select Shred original files if you want to securely delete
from your system the files/folders you are putting into
the 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.

When you have specified the files/folder you want
included in the PGP Zip archive, click the Security tab.

9

Click Save.

10 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).
11 Enter the appropriate passphrase, then click OK. The
PGP Zip archive is created in the location you specified.

Using PGP Shred to Shred Files
6

The PGP Shredder feature completely destroys files and
folders so that even sophisticated file recovery software
cannot recover them. While both the PGP Shredder icon and
the Windows Recycle Bin (on Windows systems) or the Trash
bin (on Mac OS X systems) appear on your desktop, only PGP
Shredder immediately overwrites the files you specify so that
they are not recoverable.

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.

You can shred files using any of the following methods:

10

ƒ

Using the PGP Shredder icon.

ƒ

Using the PGP toolbar.

ƒ

Using the Shred menu option in PGP Desktop.

ƒ

Using the Finder.

confirmation dialog box is displayed, asking you to
confirm that you want to shred (secure delete) the listed
files and/or folders.
3

Shredding Files using the PGP Shredder
icon

Technical Support

To shred a file or folder using the PGP Shredder icon
1

Locate the file or folder you want to delete securely.

2

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.

3

Click OK. The file or folder is deleted from your system
securely.

Click OK. The file or folder is securely deleted from your
system.

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.

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).

Symantec’s support offerings include the following:
ƒ

Shredding Files using the Shred Files Icon
in the PGP Desktop Toolbar

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

ƒ

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

To shred a file or folder using the PGP Desktop Toolbar

ƒ

Upgrade assurance that delivers software upgrades

ƒ

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

ƒ

Premium service offerings that include Account
Management Services

1

Click the Shred Files icon in the toolbar.

2

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.

3

For information about Symantec’s support offerings, you can
visit our Web site at the following URL:

Click OK. The file or folder is securely deleted from your
system.

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.

Shredding Files using the Shred
Command from the File menu

Contacting Technical Support

To shred a file or folder using the Shred command
1

Select File > Shred.

2

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.

3

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.

Click OK. The file or folder is securely deleted from your
system.

When you contact Technical Support, please have the
following information available:

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.

2

Ctrl+click the file or folder (or right-click it if you are
using a two-button mouse) and select PGP > Shred. A
11

ƒ

Product release level

ƒ

Hardware information

ƒ

Available memory, disk space, and NIC information

ƒ

Operating system

ƒ

Version and patch level

ƒ

Network topology

ƒ

Router, gateway, and IP address information

ƒ

Problem description:
ƒ

Error messages and log files

ƒ

Troubleshooting that was performed before
contacting Symantec

ƒ

Recent software configuration changes and network
changes

Copyright and Trademarks
Copyright (c) 2012 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.

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:
ƒ

Questions regarding product licensing or serialization

ƒ

Product registration updates, such as address or name
changes

ƒ

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

ƒ

Latest information about product updates and upgrades

ƒ

Information about upgrade assurance and support
contracts

ƒ

Information about the Symantec Buying Programs

ƒ

Advice about Symantec's technical support options

ƒ

Nontechnical presales questions

ƒ

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

12



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