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Prepare for Windows 7 in Three Phases

Gartner RAS Core Research Note G00170151, Stephen Kleynhans, 1 October 2009, RA2 07182010
Many organizations are skipping Vista and looking forward
to Windows 7. This research provides the necessary steps to
prepare for Windows 7 and ensure a successful migration with
adequate operating system (OS) support.
Key Findings
• Preparation is essential for a successful migration. Most organizations will require 12 to 18
months to prepare for a Windows 7 migration.
• Organizations that have tested or prepared for Vista and have good management systems
and processes could complete the preparation process in 12 months.
• Complex environments will face additional issues and require more time.
• Allocate sufficient time and resources to upfront activities to lower the costs during
• Although your planned migration may be more than a year away, don’t delay the initiation
of the preparation process.
• Form a project committee that includes members from each major business unit, as well
as operational groups in the IT organization, to oversee the development of a project
timeline that features high-level milestones and estimates required resources.
• Establish a formal, comprehensive and workable testing methodology to ensure that
issues are identified and categorized.
• Plan on piloting for a minimum of three months. The shorter the pilot, the more problems
will occur during the deployment.
The tepid corporate response
to Windows Vista indicates
that, for most organizations,
Windows 7 will be the first
major OS migration project in
more than six or seven years.
As they start their projects,
many organizations are unsure
how to approach the planning
and testing process. Given that
proper preparation is essential
for a successful migration,
enterprises should allocate
sufficient time and resources to
upfront activities. For most, this
will take between 15 and 18
months, although some well-
organized companies could
trim the time to 12 months.
More-complex environments
will undoubtedly cause
additional issues that will need
to be addressed and added to
the plan. It’s important to get started early and regularly review
timelines and plans.
For the most part, we assume that organizations have not made
any significant progress with Vista preparations and migrations.
Organizations that have done some preparation for Vista should
find that most of their efforts are directly applicable to Windows 7,
so they will be able to reduce their overall timelines (see Figure 1).
1.0 Preparation and Education: Three Months
Organizations should establish a project committee and develop
an overall project timeline. The project committee should include
members from each major business unit, as well as operational
groups from the IT organization. The project timeline should include
high-level milestones and estimates of required resources.
Companies must obtain a detailed inventory of the user
environments, including hardware, software and processes.
Without this, planning and testing will be hit-or-miss, based on IT
perceptions, rather than reality. Although many companies have a
general handle on the PCs in their environments, most have more
difficulty with the other components. A full inventory will include the
following areas:
1.1 PC Hardware
Although organizations should primarily install Windows 7 on new
equipment, having a complete inventory sizes up the problem and
provides guidance as to the order in which users are likely to be
migrated. Organizations that have skipped Vista will probably need
to perform some forklift upgrades, and will find that a detailed PC
hardware inventory is even more essential. The inventory will also
help identify deviations from corporate standards, and should
identify where user data is being stored.
Along with basic configuration, age and model information, the
inventory should also include more-detailed data (for example,
BIOS levels, memory and disk space), as well as installed
components (for example, adapter cards and chipsets). The
Windows 7 Hardware Assessment tool can help identify potential
issues. For the most part, systems purchased since early 2007
(machines that were released after the introduction of Windows
Vista) should have no problems running Windows 7, unless they
were poorly configured.
Decide which machines to upgrade based primarily on their age
and secondarily on their configurations. If PCs purchased in 2009
and 2010 are chosen for upgrade to Windows 7 in 2011, their
configurations won’t really matter. Unless your migration costs are
extremely low, don’t plan to upgrade any PC that has less than two
years of useful life left before replacement.
1.2 Attached Peripherals
Even when PCs are replaced, attached devices are frequently
retained. These may include monitors, specialized keyboards and
mice, external storage devices, printers or other items that require
supporting drivers. Business-critical devices (i.e., essential to the
completion of a business function) should be identified. Fortunately,
most devices supported on Windows Vista carry that support
directly to Windows 7. This means that, for most organizations,
only older legacy devices are likely to pose an issue for Windows 7.
Device driver compatibility should be somewhat less of a problem
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Figure 1. The Three Phases of Preparation
Source: Gartner (October 2009)
Three months
Six to nine months
Pilot Testing
Six months
Getting ready will take 15 to 18 months.
Don't wait — get started now on the first steps.
• Hardware
• Peripherals
• Applications
• Utilities
• Processes
• IT staff
• Architects
• Developers
• Key team
• Lab testing of
• Set standards
• Create images
and test
• Develop processes
• Alpha test
• Beta test
• Cross key
business events
with Windows 7 than it was initially for Vista. Only a complete
inventory of peripherals can expose potential problems. If your
plans include installing 64-bit Windows 7, expect to find more
legacy devices without suitable drivers. This will require budgeting
for their replacement, and adding time to allow for the additional
1.3 Applications
A software inventory must include all applications and utilities
installed on corporate PCs. Many software inventory tools exist,
including Microsoft’s free Application Compatibility Toolkit (ACT)
5.5. It is not sufficient to restrict testing to “formally supported”
applications, because users’ opinions may differ significantly from
those of the IT organization, resulting in substantial delays during
implementation. All applications should be categorized into four
buckets: business-critical, user-critical, support tools/utilities and
all others. A weighting should be added that establishes each as
broadly deployed, narrowly deployed or specialized. All business-
critical applications must be determined to work on Windows 7,
while all user-critical applications must operate or have reasonable
workarounds. Because most support tools will require a new
version after an OS change, replacements or upgrades must be
identified for each utility.
1.4 Processes and Procedures
Although not typically considered an asset, the processes and
procedures that an organization has created to make the user
environment functional are likely to be affected by an OS change.
Hence, it’s critical that organizations document all the processes
associated with outfitting their users. This should also include a list
of policies, including group policy objects (GPOs).
During this initial phase, organizations should create a testing
facility/laboratory. It should include a representative sample of
systems expected to be used with Windows 7 throughout the
organization. Although it’s impossible to have one of everything,
any hardware combination used by more than 5% of the user base
or part of a business-critical function should be represented.
During this phase, key members of the technical team should
begin using Windows 7 (final code should be available to corporate
customers in September 2009, or in August under programs such
as MSDN and Technet) as part of their daily routine, followed by
most IT staff. This leverages the most technically competent (and
least likely to be seriously impaired) employees to spot potential
problems. It also serves as an informal training ground.
2.0 Development: Three to Six Months
The replacement of the OS is an opportunity to update the user
environment and implement best practices. As such, it is good
to survey the stakeholders (e.g., user groups, developers and IT
support) to determine whether there are pain points or other issues
that must be addressed. With this feedback and the complete
inventory, four separate development areas must be addressed.
2.1 Windows 7 Administrative Environment
Organizations already using Windows Vista should find that little
change is required for Windows 7. For the most part, all GPOs and
administrative processes function the same for Windows 7 as they
do for Windows Vista, with a few additional options.
Organizations currently on Windows XP will require more-extensive
changes. Using Windows XP processes as a starting point,
organizations must identify where Windows 7 5 administration
will deviate. Organizations must examine the new features and
capabilities within Windows 7 and determine a response. They
will also need to become familiar with new GPOs introduced with
Windows 7, as well as those that came with Vista.
Determining the deployment techniques that will be used is a
critical decision. Even organizations bringing in Windows 7 on new
equipment need to review image distribution, software deployment,
and migration processes for data and settings. Organizations
should also familiarize themselves with newer options, such as
application virtualization, which might be appropriate for some
Organizations also must identify the implications of leveraging new
administrative capabilities in Windows 7 and plan to address these
issues. This goes beyond changes to the administration tools built
into the product; it extends to third-party tools that are likely to
require an update.
2.2 Windows 7 User Environment and Standards
Organizations need to determine guidelines for hardware
selection. Although Microsoft has provided general hardware
recommendations, these must be interpreted with respect to
corporate standards and procurement practices. Organizations
should review our regularly updated hardware configuration
Companies must also revisit the question of lockdown for their
user environments, given the improvements in this area provided
with Windows 7. Again, organizations that have skipped Vista
are likely to have more to do to prepare for a more locked-down
environment, but even organizations running Vista will need to
decide if any changes are required, based on the new user account
control levels in Windows 7.
2.3 Image Development
The final and most-critical piece of the development process
involves the creation of an initial master build for a corporate user
environment. This will include all the common elements included
in a corporate desktop PC (for example, major applications,
management utilities, security, and anti-malware tools and
communication tools). It will be used for initial application testing,
user pilot testing and as the basis for further customized builds.
2.4 Infrastructure impacts
Windows 7 adds a number of new networking and operational
capabilities such as Direct Access, Branch Cache or Federated
Search, which could have server dependencies and significant
networking impacts. These will require additional planning and
education to determine whether they are compatible with your
infrastructure and, if so, how to properly integrate them into the
environment. For example, the BranchCache feature may improve
your software distribution capabilities, but the content that users
access must be on Windows Server 2008 R2.
3.0 Establish a Testing Program: Six to Nine
Organizations must establish a formal, comprehensive and
workable testing methodology to ensure that issues are identified
and categorized (for example, impact, scale/scope of issue and
risk assessment). Unfortunately, most companies lack formal
assessment processes, which results in inadequate and inefficient
testing (for example, poor allocation of resources, insufficient test
scenarios and incomplete regression). This slows the migration
and drives up costs. Beyond providing assurance that the new OS
will function for users, a well-designed testing process serves as
a critical learning mechanism and development tool by identifying
the shortcomings of the proposed environment and driving the
development of workable solutions. Once the migration is under
way, a formalized testing methodology will help organizations
manage system images, application rollouts, service packs and
other major initiatives that will emerge.
Establishing a testing methodology requires setting appropriate
goals in the context of business objectives for exploiting Windows
7’s capabilities. Organizations must decide early what “successful
testing” means for different stakeholders. Although most think
of testing purely for compatibility purposes, that is only one
objective, particularly given the compatibility improvements during
the past decade. Testing provides derivative value in training
and experience; impact analysis of images, support processes
and changed configuration options; and design, including the
identification of opportunities for optimization provided by new
features of the OS. A key requirement for testing is documentation
to ensure that information gleaned from the process is recorded
and followed up.
Before the new environment is rolled out, three types of testing
must be performed: basic application testing, image testing
and environment testing. Application testing involves testing
applications’ functionality with the new OS. Image testing
includes testing a complete collection of applications and tools,
ensuring compatibility of the image with hardware platforms
and implementation tools. Environment testing evaluates the
supportability of the new environment, including the processes for
management, administration and technical support. It also includes
usability testing, gauging users’ reactions to the new environment
and making necessary tweaks to ensure that it fits their needs.
3.1 Lab Testing
It is impossible to test all combinations of hardware and software
within any major organization. Most large enterprises can pare
down the number of permutations by finding common system
patterns. For configurations that cannot be represented in the
laboratory, unless some business-critical external force is at work,
a “test in production” methodology will generally suffice, assuming
that high-level testing has been performed on similar configurations.
The way PC activation works for volume license customers
changed between Windows XP and Windows Vista (and, by
extension, Windows 7). During testing, enterprises should ensure
that they are familiar with the volume activation options and include
them in testing scenarios.
Application testing can be conducted concurrently with initial
hardware testing. For each product, a formal checklist of test
parameters and goals should be created, containing five sections:
• Installation: Does the application install cleanly or are tweaks
• Basic functionality: Does it start up, and do major functions
• Advanced functionality: Do specialized or rarely used
functions, such as macros, perform?
• Interoperation and interaction: Does the application coexist
with others, do communication and data interchange functions
still work, and has the user interface changed?
• Performance: Does the application behave differently, and have
hardware requirements changed?
Regression testing (that is, testing against previously discovered
problem scenarios) is critical to ensure steady progression to a
release candidate. Test scenarios should be built using help-desk
records and notes from previous testing exercises. Reintroducing
old problems will severely damage the IT organization’s credibility
and turn an otherwise successful implementation into a failure.
During testing, any anomaly or change from the current version
must be recorded. This implies that the tester is somewhat familiar
with the current environment.
Deeper functionality testing is likely to require the participation of
a user or a developer to create a formal script. IT groups should
prioritize the application testing order based on the breadth of
deployment, with the most widespread handled first. This will
speed up the process of shifting to full image design and testing.
Companies should also consider the ability to run applications in a
reduced-rights user environment.
One difference between Windows 7 testing and previous versions
is the availability of richer and more mature testing tools. Acresso’s
Installshield and Symantec’s Wise Installer include capabilities
to detect and mitigate conflicts between applications and the
OS. Microsoft’s ACT 5.5 has emerged as a solid tool for finding
potential issues with application and device compatibility. It can
be run on Windows XP systems to help triage the testing effort,
enabling organizations to better allocate resources during testing
and remediation. Customers should download and familiarize
themselves with the ACT.
The Microsoft Deployment Toolkit (formerly known as the Business
Desktop Deployment Toolkit) has also been expanded to include
more tools and best practices. Testing tools that continually look
for incompatibilities with new versions of Windows, as well as
Service Packs, are available from such vendors as App-DNA and
Two areas of special concern for testing that might be overlooked
are testing browser-based applications for compatibility with
IE8 and testing applications in a 64-bit environment. With Vista,
customers reported the most serious and often most difficult
to remediate compatibility problems with IE6-targeted Web
applications failing under IE7. This situation is unlikely to improve
with IE8 in Windows 7. We strongly recommend that customers
begin this phase of testing as early as possible, because
remediation efforts may require recoding or adding virtualization
to their environments. On the 64-bit front, it is likely that, by 2011,
some users may require 64-bit support for their environments.
Adding a 64-bit test environment will identify potential issues early,
and, although it will add some additional effort, it will not seriously
complicate the testing process.
Once application testing is well under way, attention must be
turned to the development and testing of system images. This
testing includes the same five categories as for applications,
with particular attention given to interaction and installation.
Image testing requires matching images to particular hardware
configurations, and is likely to demand the largest effort. Device
drivers for legacy peripherals must also be validated, especially
if you’re implementing 64-bit. Once the first few images are
completed, subsequent ones will require a minimum of three days
to create, followed by a day or more of testing.
The final area is the testing of internal processes. Many well-
established procedures and policies will need fine-tuning or outright
replacement with Windows 7. Particular attention should be given
to migration processes, moves/adds/changes and ongoing support
processes (for example, software distribution and system backup/
4.0 The Pilot Test Phase: Three to Six Months
Once formal lab testing is done, pilot testing should begin. Piloting
moves the testing out of the lab and exposes real users to the new
environment. Most pilots should consist of at least two phases.
The first should test basic builds, establish training needs, gauge
general user reaction and enable IT staff to exercise their new
Windows 7 skills. This pilot should be limited to a small group of
users (fewer than 50) that does not perform mission-critical (or
high-profile) activities, and should optimally last for 45 to 90 days.
Following this, a second, broader pilot extends the first by field
testing installation and support processes within a production
(but still closely monitored) environment. The broad pilot should
optimally run an additional 45 to 90 days to ensure that the pilot
tests extend across several different business process cycles (for
example, month-end and quarter-end). For most organizations,
a three- to four-month piloting period will be sufficient; however,
those with more-complex environments, or those that encounter
significant problems in early testing, may need to run for the full six
In many cases, organizations may be tempted to cut back on
piloting to speed the overall timeline. Although both phases of the
pilot could be completed in as little as two months, shortening the
pilot period increases the likelihood that some underlying issues
will not be encountered until the production rollout phase, when
making repairs is more disruptive.
Once the piloting process has been completed, the preparation
process is effectively completed. Organizations can then conduct
staged rollouts of the OS to their user populations. Critical to all
testing and piloting is ensuring that a suitable feedback mechanism
is in place.
5.0 Bottom Line
A formal testing process significantly smoothes the Windows 7
migration path by enabling companies to spot potential problems,
adjust designs to better leverage new features and build experience
with the nascent platform.