Migration To Exchange Online And Office 365 A Step By Guide

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WHITE PAPER
Migration to Exchange Online and
Office 365: A Step-by-Step Guide

An Osterman Research White Paper

Published May 2016
π

sponsored by

sponsored by
Osterman Research, Inc.
P.O. Box 1058 • Black Diamond, Washington • 98010-1058 • USA
Tel: +1 206 683 5683 • Fax: +1 253 458 0934 • info@ostermanresearch.com
www.ostermanresearch.com • twitter.com/mosterman

Migration to Exchange Online
and Office 365: A Step-by-Step
Guide

EXECUTIVE SUMMARY
The use of Office 365 across the globe is growing rapidly, driven by the intense sales
focus of Microsoft and its business partners, along with a clear value proposition for
organizations of all sizes. While the uptake of Exchange Online is leading the early
growth charge, there are significant opportunities for organizations to leverage the
many other components of Office 365 to re-invent productivity. In this white paper,
we present a step-by-step guide for migrating to Exchange Online and the other
capabilities available in Office 365.

KEY TAKEAWAYS
•

Growth of Office 365 is continuing apace: as shown in Figure 1, among
organizations that have made or will make the decision to migrate to Office 365,
75% of users will have access to an Office 365 account by 20171.

Figure 1
Percentage of Users Served by Email Platform
Among Organizations That Will Deploy Office 365 by 2017

For IT
administrators
who have not
been involved in
a previous
migration to
Office 365, there
is a steep
learning curve.

Source: Osterman Research, Inc.

•

Office 365 offers a significant array of communication and collaboration services
for organizations of all sizes. Once a firm has migrated to Office 365, it can take
advantage of the frequent updates to the component services in Office 365,
without the cost and complexity of managing on-premises infrastructure.

•

Migrating to Office 365 is a substantial undertaking for most firms, involving
months of pre-migration learning, planning the roadmap, mitigating issues in
current on-premises infrastructure, and the execution of the actual migration
activities. For IT administrators who have not been involved in a previous
migration to Office 365, there is a steep learning curve.

•

Microsoft offers technical capabilities to enable the migration to Exchange Online,
but next to nothing for migrating to SharePoint Online and OneDrive for
Business. Even its migration tools for Exchange Online are basic, have onerous

Some users have access to multiple email accounts, resulting in totals exceeding 100%.

Migration to Exchange Online
and Office 365: A Step-by-Step
Guide

pre-requisites, and require an uncommon depth of technical ability.
Organizations migrating to Office 365 should evaluate the migration tools
available from third-party vendors to streamline, simplify, and properly structure
their migration activities across Exchange, SharePoint, and OneDrive.
•

Every organization operating under compliance requirements or who hold current
email archives that need to be migrated without breaching archiving integrity
should definitely get expert assistance from third-party migration vendors. The
risk of being out of compliance, or breaking chain of custody in email archives is
too high to do otherwise.

ABOUT THIS WHITE PAPER

This white paper was sponsored by Datto - information about the company is
included at the end of this paper.

A STEP-BY-STEP GUIDE TO THE MIGRATION
Organizations that have migrated to Office 365 have implemented various types of
solutions and capabilities to support their use of the platform, as shown in Figure 2.

Any organization
with established
business
processes,
current onpremises
infrastructure,
and historical
data under
management
faces a
significant
planning exercise
in evaluating the
shift to Office
365.

Figure 2
Solutions and Capabilities Implemented to Support Migration to Office 365
Among Organizations That Will Deploy Office 365 by 2017

Source: Osterman Research, Inc.

STEP 1: FACE THE REALITIES OF MIGRATING TO OFFICE 365
Any organization with established business processes, current on-premises
infrastructure, and historical data under management faces a significant planning
exercise in evaluating the shift to Office 365, along with a set of discrete tasks in
actually doing so. There are numerous critical decisions to make while planning the
shift to Office 365—including how to achieve value from doing so, the approach to
take, whether to involve an external consultancy, and the selection of third-party
migration tools.

Migration to Exchange Online
and Office 365: A Step-by-Step
Guide

The migration process itself requires the appropriate mindset, approach, and a set of
technical skills, tools, and experiences that are not always readily available among an
organization’s current IT professionals—or as some early adopters have discovered,
even among external IT consultancies. Getting it right is important: if the migration
process doesn’t work perfectly, staff won’t have the ability to read and respond to
email, schedule meetings and book resources, and assistants won’t be able to
manage their bosses calendar. Just thinking of Exchange at the moment, messaging
is a mission-critical system for almost all organizations—so getting a migration right is
critical.

STEP 2: MAKE FOR HOW YOU WILL USE OFFICE 365

Office 365 provides an array of capabilities for enabling communication, collaboration,
and compliance for organizations. An early task to complete in evaluating the shift to
Office 365 is how your organization will make use of the capabilities on offer. Aspects
include:
•

Whether to cherry-pick specific capabilities from Office 365 for use, such as
Exchange Online or Exchange Online Archiving, or alternatively use most or all of
the cloud services on offer.

•

Deciding whether to embrace a hybrid approach to specific capabilities, where
some services are provided from Office 365 and complementary services are
delivered through on-premises servers (for example, some Exchange mailboxes
in Office 365 and others retained on-premises). A hybrid approach can be a
short-term route for migrating to Office 365, or a long-term strategy for
optimizing IT service delivery.

•

Once staff have new capabilities available from Office 365, how will you lead
staff to the effective use of these new tools in their work? Getting business value
from Office 365 requires creating new approaches to business processes enabled
by new tools that streamline current processes by removing inefficiencies,
creating innovation, or introducing greater effectiveness.

In addition to deciding how to use Office 365, it is essential to know if there are other
competing or complementary IT initiatives being undertaken at your organization that
might impact the scope or timeline for a migration to Office 365, such as a refresh of
end-user devices. Current litigation or in-progress evaluations of possible acquisition
targets will also directly impact on the ability to move particular mailboxes to
Exchange Online and your ability to migrate email archives.

STEP 3: PROCURE THE OFFICE 365 PLAN THAT MAKES SENSE
FOR YOUR ORGANIZATION
Microsoft offers a number of plans for Office 365, with increasing levels of capability
and service coverage. An organization that wants to use a hybrid configuration
between on-premises servers and Office 365 must select a plan that supports Azure
Active Directory to enable administration tasks and seamless identity management
between the two environments.
Other considerations in selecting a plan includes:
•

Organizations with a global footprint or strict data sovereignty requirements in
some geographies need to decide between a single Office 365 tenant or the use
of multiple tenants. While an organization can set up multiple cooperative
tenants to comply with data sovereignty and address other practical issues, a
multi-tenant approach comes with a range of complexities.

•

Organizations with fluctuating staff numbers over the year could choose to
forego the slightly cheaper plans that require an annual commitment and instead
sign up for a plan that only requires a monthly commitment. This allows an
organization to optimize its cost commitment to Microsoft, but does require

Migration to Exchange Online
and Office 365: A Step-by-Step
Guide

active management to achieve.
•

While most plans include the right to install the latest version of Microsoft Office
applications on computers and mobile devices, some Office applications are
excluded from this right. Visio Pro, Project Pro, and Power BI Pro for Office 365
are available at an additional cost over and above the base plan price.

STEP 4: COMPLETE PRE-MIGRATION CHECKS AND DEVELOP
A MIGRATION PLAN
Delivering a seamless migration to Office 365 is pretty straight-forward once all the
thinking work is done. As Microsoft says, most organizations will have to spend a lot
more time planning their migration than actually putting it into practice. Here are the
tasks to work through in checking your current environment and developing a plan
for migrating to Office 365.
•

Task 4.1. Understand the Limitations in Office 365
Every system has design limits, and Office 365 is no exception. Certain
limitations may cause issues when migrating to Office 365, while others create
ongoing issues after doing so. During migration examples include migration
throttling, maximum attachment sizes in Exchange Online, the default and
maximum retention period for deleted items in Exchange, the length of file
names for upload to SharePoint Online or OneDrive for Business, blocked file
types, and unsupported characters in file names. Most of these issues can be
mitigated one way or another, but they have to be identified first. It is also
essential to ensure that all data is backed up fully prior to the migration, and that
backup capabilities are in place as the initial set of content enters Office 365.

Remote offices
with low
bandwidth
connections can
cause problems
in migrating to
Office 365.

Post-migration issues can include Microsoft’s approach to anti-malware and antiphishing attacks, compliance and e-discovery, and the inclusion of archived email
in the same system as day-to-day transactional email. Many of the issues falling
in this category can likewise be mitigated, usually by embracing third-party tools
which give organizations greater design control.
•

Task 4.2. Check Bandwidth Availability
Migrating to Office 365 is a bandwidth-intensive task, as hundreds of gigabytes
or terabytes of data are shifted from on-premises servers to Office 365. Check
that your organization has sufficient bandwidth available for the migration, and
explore alternatives for moving current and historical data to Office 365 without
using an Internet connection. For example, Microsoft offers the option of
delivering data on hard disks directly to Microsoft for upload into the customer’s
account at an Office 365 data center, and some third-party migration tools
support faster upload to Office 365 by moving data into Azure first.
Note that Microsoft has implemented multiple data throttling approaches that
limit the amount of data an organization can upload each day, so a bigger pipe is
unlikely to unilaterally solve the problem.

•

Task 4.3. Review Bandwidth Design
Remote offices with low bandwidth connections can cause problems in migrating
to Office 365, due to the long time it takes to move data across the network
links. Understand what is in place currently across your organization, and
determine whether a higher bandwidth connection is required during and after
the migration for such remote offices.
Bandwidth design for your entire organization is worth revisiting as well, in light
of the pending migration to Office 365. If your organization does not currently
have redundant network links, it may be worth introducing those since you will
be relying on a cloud service for essential day-to-day systems.

Migration to Exchange Online
and Office 365: A Step-by-Step
Guide

•

Task 4.4. Assess Active Directory Health
Hybrid approaches to Office 365 require flawless interaction between your Active
Directory and Azure Active Directory. Assess the current health of your Active
Directory setup, and resolve any issues. Things to look for include:
o

The presence of multiple forests in Active Directory. While multiple forests
can be synced with Azure AD, it is a complex process. The recommended
approach is to have a clean OU (organization unit) structure so you can sync
only specific OUs.

The exclusion of admin and service accounts for on-premises servers from
the OU structure that is synced to Azure AD. Don’t sync AD objects to Azure
AD that are not necessary for Office 365 to function.

An established process for provisioning and de-provisioning users in Active
Directory, to add new employees, update employees when changing jobs,
and removing employees who are departing the organization. Any sloppiness
in these processes will result in added costs, security vulnerabilities, and
potential data breaches.

Task 4.5. Assess Exchange Server Health
Before migrating from Exchange to Exchange Online, check the health of your
current Exchange Server infrastructure. Any configuration problems, corruption,
or other sub-performant aspects will either degrade your migration experience or
be amplified after migrating to Exchange Online. Some specific aspects to note:
o

If you are migrating from Exchange Server 2003, note there are some
specific implications during the migration process, such as mailboxes not
being available during the migration, and that failed migrations have to be
re-initiated from the beginning; they cannot be restarted from where they
failed.

Ensure your current hardware is up to the migration challenge. While
Microsoft recommends the use of enterprise-class physical hardware for
most organizations, small firms can probably get away with virtual machines.

If you are
migrating from
Exchange Server
2003, note there
are some specific
implications
during the
migration
process.

Microsoft’s Exchange Server Deployment Assistant is a good place to start. It
analyzes your current Exchange deployment using the latest guidance and premigration requirements from Microsoft, creating a customized plan for your
organization.
For organizations shifting from a non-Exchange environment—such as IBM
Notes/Domino, Novell GroupWise, or Zimbra—it is likewise important to ensure
your current system has sufficient integrity to handle the demands of the
pending migration.
•

Task 4.6. Assess SharePoint Server Health
SharePoint is a comprehensive and complex product, and organizations who
have taken advantage of its custom development capabilities are highly likely to
need to re-think their approach to SharePoint when embracing SharePoint
Online. In assessing your current SharePoint environment, consider:
o

The use of customizations, third-party Web parts, and other design
approaches that work on-premises but are unsupported on SharePoint
Online.

The effectiveness of your content structures in SharePoint. Will you just
copy across your current structure and approach, or use the opportunity of
shifting to Office 365 to restructure what SharePoint has become?

Migration to Exchange Online
and Office 365: A Step-by-Step
Guide

•

The present and future value of content in SharePoint. Content that lacks
future value should be deleted or archived (depending on your compliance
mandates) instead of being shifted across to SharePoint Online. Clearly
making decisions of this nature will need to be done in conjunction with
content owners.

Task 4.7. Catalogue Dependencies with Other Applications
Find out which applications and systems rely on or work alongside your
Exchange environment. If you are going to change your approach to Exchange
by embracing Exchange Online, you will need to undertake remedial work to reconnect other systems. For example:
o

Scanners and multi-function machines send scanned documents to staff.
Develop a plan for pointing these devices at Exchange Online after the
migration.

On-premises email archiving systems that work with your Exchange
deployment may need to be updated or replaced for Exchange Online.

Organizations shifting from IBM Notes/Domino for email are likely to have
mail-enabled and workflow-enabled Notes applications. Figure out how you
will support this mail flow after migrating to Exchange and Outlook.

CRM systems integrate with Outlook to support customer tracking and
interaction. Evaluate how your current CRM toolset will integrate after the
migration.

Evaluate the
skills of current
IT staff to
execute the
migration from
on-premises
infrastructure to
cloud services.

Task 4.8. Availability of Skilled IT staff
Evaluate the skills of current IT staff to execute the migration from on-premises
infrastructure to cloud services, including their ability to backup and archive all
relevant content. Some organizations have IT staff who have been doing email
migrations for a couple of decades, and their battle-won expertise can often
carry across to an Office 365 migration. Other organizations no longer have
these resources readily available, and will need to engage the technical
assistance of an external IT consultancy. Note that in selecting an external IT
consultancy, ensure they have specific expertise in migrations featuring the same
setup and constraints in place at your firm; don’t blindly choose your current IT
consultancy because they may lack the specific expertise required. It is essential
to ensure that backup and archiving routines not be interrupted during the
migration given the essential nature of both activities.
Shifting to cloud services does not render IT staff irrelevant and unnecessary—it
just changes the type of job tasks they perform. Consider the retraining required
to ensure current staff can manage new cloud services that are entirely delivered
from Office 365, or in conjunction with on-premises infrastructure in a hybrid
deployment. New administration and management tools frequently streamline
the execution of these tasks over time too, and these are worthy of evaluation.
Selecting a hybrid approach creates its own set of challenges, which must be
actively managed to avoid downstream troubles. For example, there are specific
versioning requirements for Exchange Server on-premises in order to work in a
hybrid configuration with Exchange Online. Ensure the processes are established
to test, deploy, and manage the ongoing update stream.

•

Task 4.9. Assess Level of Staff Knowledge on Office 365
Office 365 makes many new capabilities available to staff through the home
page and app launcher. If staff will be expected to use any of the new
capabilities in their work, select the training resources and adoption strategies
you will leverage to lead staff to effective use. Any decisions in this task should
reference the plans you made in Step 2 above.

Migration to Exchange Online
and Office 365: A Step-by-Step
Guide

•

Task 4.10. Review Compliance Requirements
Review current compliance requirements and evaluate how you will achieve
these in Office 365. Factors to review—in collaboration with compliance officers
and your legal team—include:
o

The presence of current email archives, and whether to shift them into
Office 365, move them to a separate new archiving service, or leave them in
their current state. If moving them somewhere else is deemed the best
approach, you need to plan how to migrate without breaking chain-ofcustody, which is not a trivial issue.

The existence of encrypted customer or sensitive data, and whether this
needs to be moved to Office 365. If encrypted data is moved, how will you
do this without breaking the encryption safeguards?

The requirement for data to be physically stored within specific geographical
areas, in line with data sovereignty legislation. This may dictate where to
establish a single tenant, or push you in the direction of multiple cooperating
tenants.

Organizations without compliance requirements can move faster and more
simply to Office 365. Those with compliance mandates need a rock-solid
approach to ensure their organization isn’t opened to legal risks and financial
fallout.
•

Task 4.11. Review Data Privacy Requirements
Check the data privacy requirements for data that would be stored in Office 365.
Evaluate how Office 365 handles data that would be subject to privacy
requirements (such as social security numbers and credit card numbers), and if
the automatic encryption capabilities in Office 365 will be sufficient for your
requirements. If not, a third-party add-on encryption service may be required.

Check the data
privacy
requirements for
data that would
be stored in
Office 365.

Some organizations deliberately select the location of their Office 365 tenant to
be outside of the United States to prevent US government access to cloud-based
data under anti-terrorism legislation.
•

Task 4.12. Assess Firewall Architecture
Review your current firewall architecture, as Office 365 requires certain firewall
rules to be established. Organizations with multiple independent firewalls across
their global network will require a method of coordinating rule additions,
changes, and deletions over time.

•

Task 4.13. Develop a Migration Plan
Based on a solid understanding of the current state of your IT infrastructure, the
business goals being pursued, and the way in which Office 365 will be leveraged
to enable this pursuit, develop a migration plan. Such a plan should include:
o

The phasing of the migration, particularly the order in which departments
and divisions will migrate to Office 365. Phasing will need to be coordinated
for some users in order to ensure uninterrupted delegate access for
mailboxes and calendars. This planning for coexistence, such as planning for
uninterrupted access to the directory/Global Address List (GAL) and
free/busy lookups, will be particularly important for customers coming from
Notes/Domino.

The internal IT staff and any external IT consultants who will be carrying out
the migration duties.

The timeframes for consulting with business and content owners over
content deletion, archiving, and migration.

Migration to Exchange Online
and Office 365: A Step-by-Step
Guide

•

The products and capabilities in Office 365 that will be made available to
staff over set timeframes, such as Exchange Online, SharePoint Online,
Skype for Business, and more. Many organizations start with Exchange
Online, and once that is rock solid, introduce additional capabilities.

How you will respond to a legal discovery request during the migration,
should that happen, particularly if archived data is being migrated to a new
location.

Task 4.14. Develop a Backup and Recovery Plan
Office 365 offers only rudimentary backup and recovery capabilities for customer
use, such as the ability to retrieve a deleted mailbox item for up to 14 days
through the Recoverable Items folder (this default can be increased to 30 days),
and a way to retrieve a deleted user mailbox within 30 days of deletion. What it
doesn’t offer, however, is the more traditional concept of backing up servers and
data at a point in time, to enable recovery or roll-back under disaster scenarios,
the ability to recover individual files, or data beyond the recoverable windows.
Various third-party vendors offer backup and recovery services that greatly
extend what’s on offer from Microsoft, adding an essential level for the
management of corporate data.
As shown in Figure 3, organizations that have adopted Office 365 or plan to do
so have already decided on their archiving plans for eDiscovery and legal
purposes, as well as their Office 365 strategies.

Figure 3
Plans for Archiving and Backup Capabilities
Among Organizations That Will Deploy Office 365 by 2017

Various thirdparty vendors
offer services for
mitigating the
impact of an
Office 365
outage, which act
as a type of
insurance policy.

Source: Osterman Research, Inc.

•

Task 4.15. Develop a Disaster Recovery/Business Continuity plan
Office 365 is generally a highly-reliable service, but it has experienced several
multi-hour or day-length outages in recent years. While these make international
headlines, the more immediate issue is that staff lose access to essential services
for carrying out their work. Various third-party vendors offer services for
mitigating the impact of an Office 365 outage, which act as a type of insurance
policy. Evaluate the potential risks of losing access to Office 365 for your
organization and assess how to mitigate these to ensure business continuity.

Migration to Exchange Online
and Office 365: A Step-by-Step
Guide

STEP 5: MIGRATE TO OFFICE 365

Migrating to Office 365 is usually done across several phases, with organizations
frequently shifting user mailboxes to Exchange Online first, then migrating other
aspects of Exchange, and finally looking at the other capabilities on offer.
•

Task 5.1. Migrating to Exchange Online
Migrating to Exchange Online is an involved process, requiring a set of
coordinated activities over several months or longer—depending on the size of
your organization, and the volume of mailboxes and data to migrate. You will
need to follow the steps below:
o

Verify Connectivity to Exchange
Verify connectivity from Exchange Online to your on-premises Exchange
infrastructure. Microsoft offers a tool to ensure connectivity is enabled and
configured correctly.

Pilot Test Your Migration
Pilot test the efficacy of your preferred migration option, first using test
accounts and mailboxes, and then migrating a small proportion of real user
mailboxes. Once some real user mailboxes have been migrated to Exchange
Online, it is good to take a standing brief for a couple of weeks to see if any
issues arise. If so, you can mitigate any issues on a small number of
mailboxes for future migrations, instead of trying to rein in the issues across
a much larger number of mailboxes. Third-party backup tools can assist with
a pilot migration, such as implementing a third-party backup tool in-between
Sync Active Directory and Assign Licenses and Migrate Active User
Mailboxes.

Select the Migration Option
Select the migration option that makes most sense for your organization.
Options from Microsoft include IMAP migration (for moving only messaging
data from IMAP servers to Exchange Online), Cutover Migration (for small
organizations who want to migrate all at once in one fell swoop to Exchange
Online), and two migration options that support hybrid approaches. The
hybrid approaches enable coexistence between on-premises Exchange and
Exchange Online, either for the short-term over the duration of the
migration, or as a long term strategy to optimize between the two
approaches of providing Exchange services to organizations. Both of the
hybrid approaches have very specific pre-requisites involving the integration
of Active Directory on-premises with Azure AD. Various third-party vendors
offer migration toolsets to streamline the migration to Exchange Online, if
Microsoft’s tools are insufficient or too complicated to use.

Sync Active Directory and Assign Licenses
For organizations taking a hybrid approach, the synchronization of Active
Directory with Azure Active Directory is required because it creates the users
in Office 365. Once they have been created, assign Office 365 licenses—
such as the right to Exchange Online, SharePoint Online, and install Office
2016 on computers and devices. It is useful to implement third-party backup
capabilities prior to moving data.

Migrate Active User Mailboxes
Start migrating active user mailboxes to Office 365, in light of available
bandwidth and the data throttling Microsoft applies to migration activities.
To stay within the limits imposed by Microsoft, many customers schedule a
batch of a couple of hundred mailboxes to migrate each night. Once an
active user mailbox has been migrated, update their Exchange settings so
Outlook will automatically discover the new cloud-based mailbox. Migrating
mailboxes at this rate will take from several days to a couple of months,
depending on the number of mailboxes to migrate.

Select the
migration option
that makes most
sense for your
organization.

Migration to Exchange Online
and Office 365: A Step-by-Step
Guide

Address Unused Mailboxes
Many organizations have unused mailboxes on Exchange Server that still
contain messaging data, but for whom the user has long since departed.
Exchange Online has the concept of an inactive mailbox to support this
situation. If the mailbox needs to be moved for legal or compliance reasons,
create a user account for the mailbox and attach the two, leave the account
to sync to Azure AD, assign an Exchange Online license, migrate the unused
mailbox to Exchange Online, put the mailbox on litigation or in-place legal
hold, and then delete the user account. The user account will be deleted,
the license freed up for further use (subject to some time constraints), and
the mailbox data held until the litigation or legal hold is removed.

Recommendations to manage properly within the context of Active Exchange
mailboxes and Exchange Personal Archives:

•

Migrate Public Folders
Microsoft supports the migration of public folders from Exchange 2007 and
2010, with specific requirements on the level of service packs and
cumulative updates applied to the on-premises servers. Using Microsoft’s
approach to public folder migration requires the use of PowerShell, has
limitations on the maximum size of a migrated public folder, the maximum
number of public folder mailboxes on Office 365, and more. Organizations
falling outside of these prerequisites should evaluate the use of third-party
tools to streamline and simplify their migration.

Migrate PST Files
Organizations with PST files will need to determine what information should
be migrated into Exchange Online. This requires an analysis of content
inside PST files to identify data that may be subject to compliance
requirements, a task that legal and compliance teams will need to be
involved with. Microsoft offers an unsupported tool for migrating PST files to
Office 365, but it requires a lot of manual effort. Third-party vendors offer
tools that greatly streamline and simply the processing, analysis, and
migration of appropriate data into Exchange Online or an archive.

Migrate Email Archives
Migrating email archives is the most challenging, difficult, and risky part of
moving to Exchange Online. If you decide to move your email archives from
where they current located, you need to ensure they are moved without
breaking chain of custody—in other words, without compromising data
integrity that could see your organization subject to negative legal
repercussions. Email archives can represent a much larger amount of data
than the email in current day-to-day Exchange mailboxes, and managing the
transference of this data volume has to be incorporated into the overall plan
so as not to avoid migration delays. During migration, be aware of mailbox
size limits in Exchange Online, and ensure the archived data is migrated to
the user’s archive not their mailbox.
•

Issues surrounding “stubs” – be careful to manage the stubs with
“rehydration” to avoid unhappy end users (broken links).

•

Journal data – if it exists, important considerations to manage journal
data within the context of new Microsoft rules and remain in compliance
with regulations for record keeping.

•

Legal hold data – if it exists important considerations to manage
properly and avoid legal spoliation fines.

Organizations
with PST files
will need to
determine what
information
should be
migrated into
Exchange
Online.

Task 5.2. Migrating to SharePoint Online
While Microsoft provides some tools for migrating to Exchange Online, it doesn’t
offer any valid approaches for migrating from SharePoint Server to SharePoint

Migration to Exchange Online
and Office 365: A Step-by-Step
Guide

Online. There are a couple of manual ways that can be used for some aspects
(moving documents into document libraries, usually without their associated
metadata), but nothing intelligent is on offer. The following steps are involved:
o

Understand the Limitations
SharePoint Online is not the same as SharePoint Server, and many of the
design and customization options available for SharePoint Server are not
available for SharePoint Online. Among other checks, you will need to:
§

Examine the customizations and any custom code applied to SharePoint
Server internally, and see if they can be rolled across to SharePoint
Online. If not, can they be implemented a different way?

Review the Web parts you are using with SharePoint Server, and check
if they will work with SharePoint Online.

Check the length of file names, and if the overall URL length for
referencing a document fits within Microsoft’s recommendation of 256
characters. Remember to include any folder names in your calculations.
If they are too long, can they be shortened?

Do file names or folders include any disallowed or blocked characters,
or have lots of spaces that take up multiple characters once encoded in
the resultant URL string? If so, can these spaces be eliminated?

Count the number of files that will be moved to SharePoint Online, and
how these are structured into document libraries. SharePoint has
limitations on the total number of files that can be displayed in a
document library view. If your current document structure exceeds
these limits, you will need to restructure your document libraries and
views to stay within what’s possible.

Determine if you have extra-large files, and whether you will still store
these in SharePoint Online.

Check if the total data size you need to move to SharePoint fits within
your standard allocation, or if you need to purchase additional storage.

Archive or Delete Unnecessary Data
Organizations that have been using SharePoint for some years are likely to
have accumulated a lot of documents and other content. Instead of
migrating all content to SharePoint Online, undertake a content audit to
review content currency and future value. If you don’t need it going
forward, delete whatever you can without falling afoul of compliance
regulations, and archive everything else.

Get Single Sign-On Working
If you have retained Active Directory on-premises and are using Office 365
in a hybrid configuration, you should already have single sign-on working.
If not, get that working now.

Decide On SharePoint Online Only or a Hybrid SharePoint Setup
Like Exchange, hybrid configurations are supported between SharePoint
Server and SharePoint Online. This allows, for example, organizations to
keep highly confidential sites and documents under their direct control in
SharePoint Server on-premises, while leveraging SharePoint Online for the
intranet, general team collaboration sites, and external collaboration
experiences. Microsoft offers two hybrid search designs in SharePoint to
provide integrated search results across content stored in both SharePoint
Server and SharePoint Online.

SharePoint
Online is not the
same as
SharePoint
Server, and many
of the design and
customization
options available
for SharePoint
Server are not
available for
SharePoint
Online.

Migration to Exchange Online
and Office 365: A Step-by-Step
Guide

•

Migrate Site Collections, Sites, Libraries, and More
Migrate the underlying building blocks of SharePoint to SharePoint Online—
such as site collections, sites, libraries, and lists. Third-party migration tools
enable you to lift and shift from SharePoint Server to SharePoint Online,
while maintaining correct metadata and user privileges, and either keeping
the current hierarchical structures or re-arranging such things during the
migration. Without migration tools, moving to SharePoint Online is a
manual process of recreating new site collections, sites, libraries and lists.
Documents can be moved to SharePoint Online using drag-and-drop in
Windows Explorer, but this does not maintain document metadata (who
created it, who edited it last, when it was created, etc.). Metadata about
documents contains important signals about importance, so drag-and-drop
should only be used for low value documents. Any document that’s
important to your firm should be migrated in such a way as to ensure
metadata fidelity.

Task 5.3. Migrating to OneDrive for Business
OneDrive for Business is the new home in Office 365 for personal work files and
documents, providing employees with a cloud storage solution that can
synchronize to their devices of choice, while giving the organization
administrative oversight of these personal work files. Documents stored on file
shares, corporate desktop and laptop computers, and other devices need to be
migrated from their current location into OneDrive for Business or another new
location in Office 365. The migration steps involved are:
o

Delete or Archive What Doesn’t Need to Be Migrated
Documents that have no future value or are not subject to compliance
regulations should be deleted or archived, instead of being migrated to
Office 365.

Drag-and-Drop into OneDrive for Business
After installing the synchronization client for OneDrive for Business, users
should drag-and-drop the documents they own that are related to their work
but not associated with a wider business function into OneDrive for
Business. Users can use the OneDrive for Business sync client to upload the
folders and documents they create to Office 365, making these available for
personal use across devices and for sharing with other internal and external
people in a lightweight collaborative situation.

Migrate into SharePoint Online
Many of the documents on a file share or computer hard drive should be put
into a document library in a SharePoint Online site, not in an individual’s
OneDrive for Business folder. Documents related to a team project,
department, initiative, or any other ongoing collaborative activity should be
moved to the correct place in SharePoint Online. This restructuring of
content from years or decades of working with a file share or local storage
will be a significant undertaking for most organizations.

Once you have
migrated to
Office 365, the
ongoing
challenge is to
drive effective
use and achieve
business value
through
incorporating
appropriate
Office 365
capabilities into
day-to-day work.

STEP 6: DRIVE EFFECTIVE USE AND ACHIEVE BUSINESS
VALUE

Once you have migrated to Office 365, the ongoing challenge is to drive effective use
and achieve business value through incorporating appropriate Office 365 capabilities
into day-to-day work. An exhaustive treatment of driving effective use and achieving
business value is beyond the scope of this step-by-step paper, but key aspects
include:
•

Gaining Active Senior Executive Support
Senior executives should be making use of appropriate Office 365 capabilities in
their work, including sharing documents, managing executive meetings, and
providing updates on organizational performance and direction through blogging

Migration to Exchange Online
and Office 365: A Step-by-Step
Guide

or video briefings (using Office 365 Video). Provide mentoring to executives to
help them through the transition to Office 365, as they will set a vital precedent
for staff across the firm to do likewise.
•

Developing Departmental Champions
Identify people across your organization who can become a local champion for
the use of Office 365 in departmental activities. Provide special training
opportunities for them to explore the possibilities with Office 365, as well as
support for bringing new work activities to life in Office 365.

•

Providing User Training
Some organizations find their users do not need any training to take advantage
of Office 365, and that is likely to be true when users have previously
experienced similar systems at other organizations. However, if that is not true
of your organization, then some user training to explain why Office 365 is being
used and how it is best used by individuals and teams across your firm will go a
long way to aligning usage with intent.

•

Helping Users Overcome Problems
Users will face problems in using Office 365, and will need help in addressing
these in a timely manner. Whether it is getting Outlook to connect to Exchange
Online, troubleshooting a synchronization problem in OneDrive for Business, or
identifying when to use OneDrive for Business versus a SharePoint team site, left
unaddressed these questions will derail the effectiveness of your deployment.
Provide appropriate help channels to mitigate this risk.

•

In moving to
Office 365 it is
likely you now
have excess and
redundant
servers on hand.
Ensure they are
properly
decommissioned
so you can cease
future licensing
payments.

Retiring Outdated Equipment
In moving to Office 365 it is likely you now have excess and redundant servers
on hand. Ensure they are properly decommissioned so you can cease future
licensing payments.

THIRD-PARTY PRODUCTS AND SERVICES FOR
MIGRATING TO AND MANAGING OFFICE 365
Office 365 is a strong product offering from Microsoft, and it benefits from a rich
ecosystem of third-party add-on tools that simplify migration, extend use cases, and
streamline administration tasks. For many IT administrators, this will be their first
migration to Office 365, and using select third-party tools allows them to capitalize on
the thousands of hours of experiences that other customers have already gone
through—reaping the benefits faster, avoiding the pitfalls, and getting to value with
minimum risk. Note that many IT consultancies that specialize in migrating to Office
365 have already invested in third-party tools to enable their work. Our survey
revealed that most current or soon-to-be Office 365-enabled organizations believe
they will require the use of third-party solutions to supplement Office 365, as shown
in Figure 4.

Migration to Exchange Online
and Office 365: A Step-by-Step
Guide

Figure 4
Views on the Need for Third-Party Solution in Office 365
Among Organizations That Will Deploy Office 365 by 2017

Source: Osterman Research, Inc.

Various tools add
additional layers
of security to
Office 365, or
deepen the
capabilities
already on offer.

Firms embracing Office 365 should evaluate third-party tools that can improve their
use of Office 365. Key groupings of third-party tools, some of which are offered by
the sponsors of this white paper, include:
•

Pre-Identification of Problems
Tools that check your current environment for the presence or absence of things
that will cause issues during the migration. These include metadata consistency,
incorrect user names, permissions that have been incorrectly assigned, users
who have left the firm who still have access to corporate resources,
incompatibilities with other software, and disallowed file types, names, or sizes.

•

Simplify Migration Activities
Tools that streamline the process of migrating from current on-premises servers
to Office 365 services. For example, providing one-hop migration from a legacy
Exchange Server environment to Exchange Online, without having to upgrade to
a later version of Exchange Server first. Similarly, the ability to migrate
SharePoint and other content sources to SharePoint Online or OneDrive for
Business, while maintaining full metadata integrity. Some tools support the rearranging of content structures during the migration process, scheduling
migration activities to optimize available bandwidth, and automating staff
communications about pending migration activities.

•

Adding Security
Various tools add additional layers of security to Office 365, or deepen the
capabilities already on offer. Examples include a second layer of defense for
malware, phishing, and spam, in addition to what’s on offer with Exchange
Online Protection. Another example is more comprehensive data loss protection
that addresses Office 365 directly plus other non-Microsoft services in use at the
organization. Third-party encryption capabilities can also provide important
benefits to bolster the security available in Office 365. Finally, some tools report
on security issues with orphaned content and ex-employees who still have access
to Office 365.

Migration to Exchange Online
and Office 365: A Step-by-Step
Guide

•

Address Archiving Challenges
Tools that allow organizations to move with integrity from a current archiving
system to Office 365 (or somewhere else), with full chain of custody ensured and
compliance mandates continuing to be met. Messages that have been archived
can be reconnected to the original mailbox, so users have seamless access to
their archived messages after the migration to Office 365. Other tools add
archiving capabilities to services like SharePoint Online and Yammer, which do
not have native archiving in Office 365.

•

Address Compliance Requirements
Tools that improve the compliance capabilities in Office 365, by strengthening
encryption, extending data loss protection, and improving policy-based archiving
of content across Office 365. As one example, the use of third-party encryption
can make data more secure by encrypting data before it reaches Microsoft’s data
centers. In the event that one or more Microsoft data centers is breached, or if
Microsoft is subpoenaed by a government, customer data will still be protected.

•

Improve Backup and Reliability
Tools that enable an organization to backup content in Office 365 outside of
Office 365, either using on-premises storage or a different cloud storage
solution. Other tools ensure service reliability during outages or interruptions.

•

Streamline Administration
Tools to streamline ongoing IT administration of hybrid deployments and Office
365 services. Examples include content restructuring in SharePoint Online,
analyzing license usage, providing a single administration console that hides the
complexity of the multiple administration consoles in Office 365, and managing
the interaction between Active Directory and Azure AD.

•

Messages that
have been
archived can be
reconnected to
the original
mailbox, so users
have seamless
access to their
archived
messages after
the migration to
Office 365.

Assist with Training and Adoption
Tools that assist with training and adoption activities, such as video-based
training tutorials that can be targeted to specific groups of users.

CASE STUDIES ON MIGRATING TO OFFICE 365
MANUFACTURING FIRM IN SWEDEN

A medium-sized firm (275 users globally) migrated from Hosted Exchange (with
Rackspace) to Exchange Online, with the goal of gaining consistent licensing one of
the key drivers for the migration. Migration took place over three weeks, thanks to
the use of a third-party migration tool that handled both Exchange mailboxes and
public folders. One of the complexities during the migration was ensuring unbroken
mail flow while migrating public folders. After the migration, the most significant
challenge was providing good advice to end users on the best tool to use for which
activity, since the whole platform is not 100% ready for the enterprise. For example,
while Exchange Online works fine, newer capabilities like Skype for Business and
OneDrive for Business operate less reliably. The firm took a few lessons from the
migration too: clean your mailbox before migrating, archive email before moving to
Office 365, and communicate earlier with end users.

UNIVERSITY IN THE UNITED STATES

Migrated over three months in late 2013 to Office 365, with staff and faculty coming
from Exchange 2010 on-premises, and students coming from Live@EDU. This was
prefaced with some months of planning, in order to map out which mail systems
people were coming from and where they would end up. One significant challenge
the university has had to deal with is Microsoft’s frequent changes on direction,
licensing allowances, and recommendations on approach. For example, that students
can’t be in the tenant, and then a reversal so they could be. Or the need for
individual licenses for everyone, with a subsequent reversal and permission for a
combined license. Another significant issue is Microsoft’s approach of releasing new
capabilities with little or no communication; for example, the auto-processing of less

Migration to Exchange Online
and Office 365: A Step-by-Step
Guide

important email in Outlook into the Clutter folder has been an “unmitigated disaster”
for the university. Third, the university has found the legal hold and e-discovery
capabilities in Office 365 to be “basic and extremely painful to use.” Finally, the
quality of edge filtering in Exchange Online Protection is severely limited, and the
university is evaluating a secondary edge filtering service to add another layer of
security.

HEALTHCARE FIRM IN THE UNITED STATES

Migrated from Google Apps to Exchange Online, taking three months to migrate 75
mailboxes. Early pre-migration testing showed the IMAP migration option from
Microsoft would work fine, but on executing the migration, the firm discovered
various problems that required subsequent rounds of migration activity. The firm also
found that resource bookings and conference rooms didn’t migrate properly from
Google Apps, necessitating the creation of a fresh set of resources and the
rescheduling of affected meetings. In light of these issues, the firm would put more
effort into pre-migration testing and analysis, in order to decrease negative impacts
for users.

UNIVERSITY IN THE UNITED STATES

The university migrated from GroupWise to Office 365, in order to move from a
capital expenditure model to an operating expenditure one. The university ran both
systems side-by-side for a while, with email forwarding rules established from
GroupWise to Office 365. Students were cut across to Office 365 over a weekend,
while staff and faculty were migrated department-by-department over a 6-month
timeframe. The university used a third-party migration tool, but it was nonperformant until sufficient virtual machines were put in place to provide multiple
channels for migration. Challenges during migration included throttling by Microsoft,
errors in appointment times after migrating to Exchange Online, and poor support for
IMAP clients against Office 365.

Office 365
provides a strong
alternative to onpremises
infrastructure for
some
organizations,
and a strong
complementary
story for many.

HEALTH INSURANCE FIRM IN THE UNITED STATES

Migrated from IBM Notes and Domino, IBM Connections, and IBM Sametime to Office
365, with Exchange Online the initial focus, followed by Yammer and SharePoint
Online. After resolving issues with Microsoft’s compliance agreement for health care
organizations, the firm migrated 5,000 employees using third-party migration tools
over six months. With Notes applications still sending email, a connector was needed
between Domino Directory and the new Active Directory, to ensure seamless mail
flow as the environment changed. Looking back on the migration, one thing the firm
would do differently is to include an Office 365 Desktop Specialist on the team, to
help end users get up-and-running quickly and efficiently. Consultants from the
Microsoft Business Partner firm engaged to help with the migration had good serverside capabilities, but the client-side issues floundered, causing at least three months
of additional time during the migration. Other issues that had to be resolved included
a new way of encrypting email (Microsoft vs. IBM), the requirement for new firewall
rules, and data throttling while migrating users. Finally, given the pace of change in
Office 365, the firm believes that keeping track of pending changes and the
implications for the firm is a full time job for an employee.

CONCLUSIONS AND RECOMMENDATIONS
Office 365 provides a strong alternative to on-premises infrastructure for some
organizations, and a strong complementary story for many. Microsoft is better
positioned to deliver cost-effective email services in Exchange Online than most
organizations can deliver through Exchange Server. Organizations with different email
servers are migrating to Office 365; it is not just limited to Microsoft shops.
There are a lot of tasks to sequence correctly and get right in migrating to Office 365,
and almost all organizations will be able to migrate with less complexity and cost by
using third-party migration tools for Exchange Online, SharePoint Online, and

Migration to Exchange Online
and Office 365: A Step-by-Step
Guide

OneDrive for Business. Third-party tools for migrating to Exchange Online streamline
the migration process and improve flexibility. Third-party migration tools for
SharePoint Online and OneDrive for Business can mitigate file naming and metadata
issues during the migration, and provide ongoing content structuring and
management tools.
While Office 365 is a competent service offering that is being updated frequently,
organizations should evaluate the use of complementary third-party tools to bolster
compliance, security, reliability, and archiving capabilities in Office 365. Some
capabilities are not offered in Office 365 at all (e.g., backup), and organizations will
need to look to third-party vendors to address this limitation.

SPONSOR OF THIS WHITE PAPER
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2015 McChord was named to the Forbes “30 under 30” ranking of top young
entrepreneurs.

Migration to Exchange Online
and Office 365: A Step-by-Step
Guide
© 2016 Osterman Research, Inc. All rights reserved.
No part of this document may be reproduced in any form by any means, nor may it be
distributed without the permission of Osterman Research, Inc., nor may it be resold or
distributed by any entity other than Osterman Research, Inc., without prior written authorization
of Osterman Research, Inc.
Osterman Research, Inc. does not provide legal advice. Nothing in this document constitutes
legal advice, nor shall this document or any software product or other offering referenced herein
serve as a substitute for the reader’s compliance with any laws (including but not limited to any
act, statute, regulation, rule, directive, administrative order, executive order, etc. (collectively,
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Subject                         : Migration to Exchange Online and Office 365: A Step-by-Step Guide
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