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 Windows Migration Tips, Tricks, and Gotchas An Olenick & Associates White Paper March 2013 

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Windows MigrationTips, Tricks, and Gotchas

An Olenick & Associates White Paper

March 2013 

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Windows Migration Tips, Tricks, and Gotchas

Contents

Introduction ................................................................................................................................ 1 Plan and Prioritize....................................................................................................................... 2 Check Hardware and Software Compatibility ............................................................................. 3 Pre-Test Application Compatibility ............................................................................................. 4 Benchmark Existing Performance ............................................................................................... 5 Fine Tune your Approach ............................................................................................................ 6 Prepare and Test Installation Packages ...................................................................................... 7 Don’t Throw Users into the Deep End......................................................................................... 8 Conclusions ................................................................................................................................ 9 About Olenick & Associates ........................................................................................................ 9 

Copyright © 2013 Olenick & Associates, Inc. All rights reserved.

205 W. Wacker Drive, Suite 2000

Chicago, IL 60606

312 332 0096

http://olenick.com 

@OlenickIT 

Additional copies of this white paper can be downloaded from

http://olenick.com/Windows-Migration-Tips-Tricks-and-Gotchas.pdf 

Windows is a registered trademark of Microsoft Corporation in the United States and other 

countries.

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Windows Migration Tips, Tricks, and Gotchas 1

INTRODUCTION

Microsoft is offering carrots and sticks for Windows XP or Vista users to migrate to either

Windows 7 or Windows 8. If you’re in that situation, you have plenty of company. As of January2013, about 43% of all Windows personal computers are running XP; 6% are still running Vista

or earlier Windows versions.1 

While the basic steps to upgrade a single PC are straightforward2, there are pitfalls.

Deciding what to data to keep, making copies, uninstalling apps, installing a new OS, re-

installing apps, and copying over user data files can take even a moderately technical user

several days. For an organization that relies on hundreds or thousands of PCs, this presents a

significant operational challenge.

Olenick & Associates has helped our clients migrate over 40,000 PCs to Windows 7 or Windows8. In this white paper, we share some tips from our experience about how to plan, prepare, and

conduct a Windows migration for a large number of PCs. * 

  Plan and Prioritize

  Check Hardware and Software Compatibility

  Pre-Test Application Compatibility

  Benchmark Existing Performance

  Fine Tune your Approach

  Prepare and Test Installation Packages

 Don’t Throw Users into the Deep End 

We’ve also found that following this sequence helps to minimize migration detours,

backtracking, and dead-ends.

*You may also be interested in our companion white paper, How to Pull the Windows Migration Trigger:

Five Questions Every CIO Must Ask. 

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Windows Migration Tips, Tricks, and Gotchas 2

PLAN AND PRIORITIZE

A successful migration begins with creating a detailed roadmap for your organization and then

translating that into an action plan.

Spend plenty of time

analyzing your

application and

hardware census

Identify every PC that needs an upgrade.

Create a complete list of who uses which applications. This

will drive compatibility testing, packaging, and deployment.

This also defines the scope of the project.

Define migration

priorities and focus

About 20% of the applications will consume about 80% of 

the time and effort.

Identify and prioritize the applications that are most likelyto have problems and start working on them as soon as

possible.

Look at native

platform capabilities

versus the need for

third party utility

products

Third party utilities are most likely to have compatibility and

support issues.

Reducing the reliance on third parties will reduce the time

needed to find fixes and make deployment more stable.

Contact vendors early

about compatibility

Vendor compatibility support may take some time andcould affect the migration schedule.

Some vendors may be unwilling or unable to certify the

compatibility of their applications for the new platform.

Give the vendors enough time so that any upgrades or fixes

can take place as soon as possible.

Do not assume all

vendors will support

Windows 7 or 8

Some app vendors will not or cannot provide information

about the compatibility of their products on Windows 7 or

Windows 8. In this case, you may have to conduct extensive

functional testing to assess compatibility.

If you find compatibility problems, the vendor may be

unwilling to resolve these problems.

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Windows Migration Tips, Tricks, and Gotchas 3

CHECK HARDWARE AND SOFTWARE COMPATIBILITY

Each PC, application, and peripheral variant may have compatibility problems in your new

environment. Alternatively, some may require special handling during the migration. Try to

discover these problems with early testing and take corrective steps long before you attempt

the first conversion of a user’s PC. 

Review and test

application and

peripheral compatibility

as soon as possible

Hardware support can often lag application support,

especially for older or special purpose peripherals.

Legacy peripherals (printers, displays, print/fax combo,

etc.) may not be compatible with upgraded or

replacement applications.

Early identification of these problems reduces the risk of 

delays and wasted effort.

Some fixes may require significant lead-time and effort to

identify and then provision replacement peripherals.

Don’t assume existing

peripherals are

compatible

Just because a device works with the current OS on the

current PC does not mean it will work on the same PC

with the new OS, or with a new PC and OS.

New hardware probably will not have legacy hardware

interfaces like nine-pin serial or parallel ports.

Device drivers for older peripherals may not be available

for Windows 7 or 8.

Don’t forget to check

multi-function devices

Legacy multi-function devices (print/scan/fax combo, etc.)

that work on XP are likely to be incompatible with

Windows 7 or 8.

Do not set project

timelines until you

complete your

compatibility

assessment

The time needed to fix compatibility issues can have a big

impact on schedule.

You'll have better odds of meeting schedule

commitments if you set your timeline after completing

your initial compatibility assessment.

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Windows Migration Tips, Tricks, and Gotchas 4

PRE-TEST APPLICATION COMPATIBILITY

Once you’ve worked out configuration-related issues, it’s time to set up some PCs with the new

configuration and then use them to test if the migrated apps will actually run.

At best, only half of 

applications that run on

Windows XP will run on

Windows 7

Although many applications that run on XP will also

run on Windows 7, many will not. Some that can run on

Windows 7 will not run on Windows 8.

Network connectivity or application configuration

issues often cause problems.

Look out for IE 6 zombies

Internet Explorer 6 will not run on Windows 7 or 8.

Although most users have long ago upgraded or

switched browsers, legacy intranet web servers and

web content may be hard-coded for IE 6. These web

sites will have to be reworked.

Use application

compatibility tools

Tools like Microsoft’s Application Compatibility Tool

(ACT) and Flexera’s AdminStudio automate initial

compatibility testing. This saves a lot of time and

quickly identifies applications that are most likely to

have problems.

DOS applications will not

work under Windows 7 or 8

Most DOS programs were written for 16-bit hardware

and the FAT file system. These applications often areincompatible with 32 and 64 bit PCs. Most of these

applications will have to rewritten or replaced.

Don’t forget this also applies to apps running on

Windows 95 or Windows 98, which are based on

MS/DOS, not NT.

Pay particular attention to

applications that mustinteroperate with one

another

It is very likely that applications used together but

provided by different vendors will have support and

compatibility issues.

It is possible that one of the applications is compatible

but others are not.

Getting these applications to work together may take

more time than you might think.

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Windows Migration Tips, Tricks, and Gotchas 5

BENCHMARK EXISTING PERFORMANCE

Users’ expectations for how long their PC takes to do just about anything play a big role in how

the result of a migration is perceived. We’ve found it is very useful to establish a credible

baseline of an existing environment’s performance. This helps to identify problems with

converted PCs, evaluate complaints about the new environment, and substantiateimprovements.

Benchmark results have a

significant value in

assessing impact of future

deployments

Users have expectations for application performance. If 

an application appears to run slower on upgraded PCs,

they will assume there are problems and could

potentially reject the upgrade.

Benchmarking can also identify and trouble-shoot

performance issues before deployment.

Return on investment in

developing automated

tests is quickly realized

when scripts are designed

for future testing efforts

Automated benchmark test scripts can be used

repeatedly during the application’s life cycle.

Application service packs, operating system upgrades,

hardware changes, and network changes can affect

performance.

Developing re-runnable performance test suites will

save time when you need to re-run performance tests

after making changes for any reason.

Use Windows PERFMON

metrics to identify

performance problems

Older PCs may not have enough memory or a fast

enough CPU for adequate performance with the new

stack.

Microsoft’s PERFMON metrics can indicate PC

hardware limitations and provide evidence that

hardware upgrades are (or are not) needed.

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Windows Migration Tips, Tricks, and Gotchas 6

FINE TUNE YOUR APPROACH

Details matter. Even something as simple as a bad choice for file and folder names can

necessitate an installation do-over, leading to headaches and wasted effort.

Include as many

applications as practical

in the base image

The base image is installed on every PC.

This should include as many applications, tools, and

components as possible to cut down on the amount of 

time that will be needed to deploy and setup individual

PCs.

Chose a default

document file type early

Will you default to using the older file types (.doc, .xls,

.ppt, etc.) or newer types (.docx, .xlsx, .pptx, etc.)?

The defaults for files and documents will be set as part of the base image. Therefore, the applications and tools

needed to support the defaults must be part of the base

image.

Setting associations early on will reduce testing and

debugging time, avoiding wasted effort and delays.

Define and follow aconsistent version

control approach for

images

The base image includes the Windows OS, components,

tools, and applications that everyone will get.

During the development process, the image will have tobe adjusted to meet compatibility needs. Proper version

control and distribution is critical to testing and problem

solving.

Working with an out-of-date image will lead to wasted

time and frustration that will affect the schedule and

budget.

Create and maintain atest repository for up-to-

date status and

transparent reporting

It is critical that all project members have access to the

most accurate and up-to-date information

A central repository for all test assets and test run results

is vital to a smooth workflow.

Accurate tracking of compatibility test results will avoid

delays in issue resolution and prevent non-compatible

applications from being deployed.

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Windows Migration Tips, Tricks, and Gotchas 7

PREPARE AND TEST INSTALLATION PACKAGES

Packaging is the creation of installation files for the new OS and applications, typically in the

MSI or App-V formats. Packages will greatly facilitate the installation of your applications.

However, packages can be tricky to get right. You cannot be sure they’ll work until you testthem on PCs built with the new baseline image.

Allow extra time for

adequate packaging andpackage testing

Organizations that have deep experience with XP or Vista

often lack of technical resources and Windows 7 or 8

packaging expertize.

In addition, the absence of clear documentation or wide

variation in existing configurations can lead to missing

package components.

Packaging will most likely require more time and

resources than might be assumed at first.

Improper packaging can lead to many application

installation issues. Repackaging to correct these issues

can cause delays.

Different configurations

will have unique

compatibility problems

Image problems are common for

  Java and .NET versions

  Adobe Reader (PDF’s) and Crystal Reports

  Base Windows 7 image

All applications will need to use the same versions of all

the components, add-ins, and tools. Insuring that all the

applications are compatible with the same versions will

require extra effort in issue resolution with the

application and component vendors.

Do not assume all applications will work with the same

versions of the tools, frameworks, or Java runtimes. This

can be one of the hardest and time-consuming parts of 

the migration effort.

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Windows Migration Tips, Tricks, and Gotchas 8

DON’T THROW USERS INTO THE DEEP END

A Windows migration project will probably affect every user in your organization — it is high

risk and high visibility. Your user community probably will not care about the finer points of 

Windows technology, but rest assured they will care if their workflow is disrupted.

A certain level of disruption is inevitable for a migration and will be tolerated. However, any

problem that is seen as unnecessary or a result of sloppy execution will lead to trouble.

Communication, education, training, and ongoing support should therefore be part of your

migration approach.

Resolve configuration,compatibility, and

package issues prior to

engaging users

Thorough testing of configurations, images, and

packages prior to involving users will prevent many

problems and delays.

When users are brought in for user acceptance testing

(UAT), any issues they find could result in rejection of the

upgrade and bad feelings.

If the users get a bad first impression, they will be less

inclined to cooperate in further retesting and final

acceptance.

Involve the packaging

team to sort out delivery

problems from functional

problems

When doing user testing, users are often confused about

what is causing an issue. They may be unable to

determine if an issue is an application functional problem

or if the application was not installed and set-up properly.

A technical person must be available to trouble-shoot and

identify the source of the problem.

It is especially important to involve the packaging team

to insure the intended installation was done properly and

that installation issues are not masking other problems.

Have a technicalcoordinator triage and

validate user acceptance

testing issues

Resolving issues in UAT can have a direct impact on a

deployment schedule. User issues are often a result of 

unfamiliarity with the new configuration.

Have a person or team with both application knowledge

and technical skills coordinate and triage UAT issues. This

will help reduce the impact of issues found and keep the

testing progress on track.

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Windows Migration Tips, Tricks, and Gotchas 9

CONCLUSIONS

Although the objectives and basic steps for a Windows migration are straightforward, scaling

the process to an entire organization presents many challenges.

In this white paper, we’ve shared some of the practical and technical lessons we’ve learned in

supporting all aspects of migration on over 40,000 PCs.

A complete census, thorough compatibility testing, and careful planning will avoid waste and

delays. Early compatibility, configuration, and package testing are keys to success. Early

performance benchmarking helps to prevent problems and resolve rollout issues. Orchestrating

user testing and support to minimize snags will facilitate user acceptance.

ABOUT OLENICK & ASSOCIATESWe published this white paper to help IT managers and staff plan and execute a Windows

migration project.

In our experience, many underestimate this challenge. To find out more about how our Assured 

Windows Migration solution can support your migration, please contact Bill Mertes at 1 (312)

804-5793 or via email at [email protected]

To learn more about our Assured Windows Migration solution, please visit

http://olenick.com/2w7w8. 

NOTES

1 Desktop OS by Version, February 2013. Net Market Share. http://www.netmarketshare.com/ 

2For example, see

http://windows.microsoft.com/en-us/windows7/help/upgrading-from-windows-xp-to-windows-7