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Mission possible – Designing and implementing a successful windows migration to the latest version of Windows 10

(Image credit: Anton Watman /

As any IT admin with responsibility for desktop operating systems knows, planning and implementing a migration is an extremely time-consuming task. Preparing for a successful one takes an inordinate amount of time and resources.  In this article, we will look at best practices to help smooth the way.

Windows 7 and early Windows 10 OS migrations to the latest Windows 10 versions can be painful for both users and Administrators. There are many user profile changes between even versions of Windows 10 that can break profiles and cause a loss of user data when upgrading your Windows enterprise.  Windows 7 standard support expired on 14 January this year, it is possible to have extended support but it’s very expensive - $25 per machine 2020-2021, $50 per machine 2021-2022 and $100 per machine 2022-2023 for Windows 7 Enterprise. It can be up to $200 per machine for Windows 7 Pro!  Alternatively, you can obtain a three-year extension should you wish to implement Microsoft Windows Virtual Desktop (WVD) - that includes Multi-session Windows 10 and three-year Windows 7 running on WVD extended support - which may be the best way forward for your organisation. If, however, you’re not yet ready to move your desktop workloads to the cloud, then following the steps outlined in this article will provide a ‘mission possible’ in migrating with the minimum of fuss. If implemented correctly, you can also ensure the holy grail of zero-downtime for your users!

Top three considerations

In any OS migration, there are three key considerations: Users, Applications and Hardware.  Let’s work through each step separately.


Remember, users are IT’s most important customers, so the first step is to identify which users to migrate first.  You also need to consider how to protect user-authored data and to keep it secure and accurate. Ensure you capture user profiles from the legacy Windows OS accurately and efficiently to keep users productive during the migration. It is highly recommended to ‘baseline’ current user experience so that you can provide empirical data to demonstrate the new OS is performing as well as, if not better than, the old version.  We’re all too familiar with ‘level-8’ of the OSI stack, whereby a user reports: “It worked much better before!”

We highly recommend using a profile management solution that is dynamic as Windows OS changes can break profiles – and copy/paste methods are inefficient and do not scale.

The ultimate goal is to make the migration as frictionless as possible – for both the IT teams and the users. However, as many of us know, Windows 10 has not been completely stable in early iterations. We’ve seen instances of OSes literally blowing up so you MUST ensure your user profiles are portable to provide you the option – should you need it – to go back as well as forward should a situation like this arise.


These really are the ‘production centre’ of the desktop and thus it is essential to get an inventory of applications in use. Once you have this data, you then need to consider the compatibility of the apps running on the new OS. Indeed, your apps may not be compatible with VDI or server-based computing.  At this stage you might also want to investigate a better method of application delivery. Should you consider removing applications from the desktop image? What about application virtualisation or application layering? OS migration is a good time to rethink your application delivery strategy.


Again, the first step is to get a complete inventory hardware devices/OSes in use and determine their compatibility with the new OS.  You should also size storage at this stage for profiles and user data. This is also a good time to consider the potential of moving some workspaces to a virtualised environment.

You need to determine which of your enterprise hardware end points are capable of running the latest versions of Windows 10. While early version of Windows 10 were not as CPU and RAM hungry as Windows 7, that has changed over the years. Taking a guesswork approach will not suffice. There are purpose-built assessment and user experience software solutions that are ready for the task. Essentially, these solutions monitor the user experience and usage with a small agent in the Windows OS for a minimum of two weeks. At the end of that period you’ll be able to generate straightforward results on a group by group or machine basis that will easily identify hardware that is up to the task of running the latest version of Windows 10. Once your users have made the switch to Windows 10, many of these solutions can monitor the success of your project and help diagnose negative user experience trends before they become problems.


In conclusion, to ensure a successful migration, follow these steps below and you’ll be ready for “Mission Possible”, whatever migration task is thrown your way.

  • Assess legacy desktops and applications – design, right-size environment
  • Leave no mission-critical data behind – harvest user-authored data and user profiles
  • Windows 10 OS – prepare your base/golden image or traditional install
  • Applications – in the golden image, application layering, or traditional install
  • Ensure user data availability – user-authored data and user profiles available in new environment
  • User-authored Data – files backed up to media or folder redirection
  • Monitor user experience – validate and monitor the user experience for QA

Jason E. Smith VP of Windows Solutions, Liquidware

Jason E. Smith
Jason E. Smith is VP of Products at Liquidware and directs the strategies for the company's innovative desktop solutions. Jason frequently speaks on desktop computing technologies at industry events such as Citrix Synergy and VMworld.