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Migrating users to Windows 10: Overcoming profile, data and app challenges

Windows 10 is here and there are many indications that it will be quickly adopted by consumers and enterprise customers alike. With a new look, the reintroduction of the Start Menu, and new features, it holds the promise of a quicker and more productive Windows desktop.

While many organisations will tread with caution, having been bit by bugs and a loss of user productivity in both Windows Vista and Windows 8/8.1, Windows 10 seems to have everyone excited about moving to the new Windows OS as soon as possible.

Since the introduction of Windows 7, Microsoft hasn’t exactly made it easy to bridge users over to new OSs. The primary challenge is created by Microsoft itself by intentionally, for technical reasons or perhaps carelessly, “breaking” the compatibility of Windows profiles between OS versions.

For this reason it has long been a monumental task to migrate users to a new Windows OS. It’s also a risky proposition to migrate to a new OS before it’s proven. The last thing organisations want to do is risk user downtime or a loss in productivity because an OS is unproven. Migrating to a new OS is indeed a big decision, but doesn’t have to be.

Proven technology has been developed to ease the burden of user migrations, in fact certain technologies can end migrations for end users altogether. Three key challenges exist for getting a user to a new Windows OS:

  1. Harvesting and injection of the user profile to ensure no loss in productivity for users
  2. Harvesting and availability of user created, user authored data
  3. Application compatibility and delivery for the new Windows OS.

User Profiles

Microsoft User profiles contain individual user settings, ranging from desktop backgrounds and window sizes to web browser bookmarks, spellchecker dictionaries, Outlook/mail signatures, Offline and Personal mail folders, contact names and addresses, accessibility configurations, and much more.

User documents, cloud storage repositories and so forth are also typically stored in the user profile. Organisations that think it’s smart to rip and replace profiles with a blank Windows created profile should carefully think it through. By many calculations, losing a Windows profile can cause each user affected a loss in productivity of 8 hours or more and can cost an organisation millions in lost data that may have been stored in the users’ profile.

Unfortunately for users, Microsoft has changed the location of where user profiles are stored with every new Windows release since Windows 7 and Server 2003. As a result Microsoft has broken the compatibility of User Profiles between OS versions for the past X versions and they have done it again with Windows 10. Take a look below at Windows version numbers and introduction of a new of Microsoft Profiles at every release along the way.

Windows Desktop OS Windows Server OS Profile Version #
XP Server 2003 v1
Win 7 Server 2008 v2
Win 8 Server 2012 v3
Win 8.1 Server 2012 r2 v4
Win 10 ? v5

Microsoft User State Migration Tool (USMT) tool offers little assistance to the problem. USMT mandates that users’ experience downtime during the conversion process, is very cumbersome to automate on an enterprise wide scale, and is a one-way only process that converts a profile forward but cannot make it compatible or co-exist with older Windows versions. Many organisations have multiple versions of Windows, including traditional desktops and virtual - Citrix/VMware/RDSH - desktops that need to co-exist for a period of time of perhaps just retain the capability until upgraded.

There are User Environment Management (UEM) software solutions on the market that will get your users under management today in the legacy environment by making their profiles compatible with virtually any version of Windows profile. Implementing a qualified UEM solution today will make it easy on both users and Administrators to make the switch. Choosing the right solution will manage user profiles and data separately from the Windows OS and will end Windows migrations for users in the future. Please read the summary checklist at the end of this article for additional recommendations.

User Authored Data

Users tend to store data in their User Profile within Windows. Industry-wide best practices are to provide a network redirect key user profile Shell Folders like “My Documents” and the “Desktop” folder – folders where users are likely to store data. But what if these folders have not been redirected? To make matters worse, users may store user authored data anywhere in the user profile and applications that are not well-written may be designed to save data and user authored files to the user’s profile. A few examples include Microsoft Outlook local files and Contacts, Lotus Notes, and many software accounting packages.

User authored data is obviously of utmost importance to most organisations, therefore the time to plan and implement a migration strategy is while the legacy environment is still live. Don’t make the mistake of turning off users’ desktops too early, only to find out they have mission critical data that has been lost to the old environment. Please read the summary checklist at the end of this article for additional recommendations.

Applications and User Experience

Aside from the migration of the user profiles and user authored data, there are other considerations for migrating users to Windows 10. For example, it is critical to perform an application assessment to know which applications need to be move/installed/layered/or virtualised into the new environment. It is also important to baseline user experience before, during, and after migrations so you can prove the new environment is better than the last, as well as grow and scale the new desktop environment accordingly.

In the end, proper planning and execution is the key to a successful user migration. Below is a recommended checklist for a successful Windows 10 migration.

Checklist to ease Windows 10 Migrations

  • Prepare the legacy environment for migration readiness
    1. Ensure you use a qualified third-party solution that makes profiles seamlessly compatible across Windows OS versions. Choosing the right solution will manage user profiles and data separately from the Windows OS and will end Windows migrations for users in the future.
    2. Redirect key shell folders per best practices. These include, but are not limited to, My Documents, Desktop, and Pictures. Some UEM solutions will handle this for you.
    3. As part of folder redirection for User Authored Data, ensure you have harvested user created files from users’ profiles. Some UEM solutions will handle this for you.
    4. Assess Users’ Applications, usage patterns, and hardware. Know which applications will be needed in the new environment by knowing which applications they actually use. Size the hardware, network, and storage in the new environment accordingly. Use this data to baseline the User Experience (UX) of the legacy environment.
    5. Plan your application delivery strategy. Now is a good time to consider SaaS applications, application layering solutions, application isolation, and server hosted published applications.
  • Ensure the new environment is delivering a better, more productive, desktop
    1. Manage Users Efficiently – The UEM solution you may have chosen to make profiles compatible can be leveraged to entitle users with context aware policies, printers, and applications. Tweaks always need to be made to a new Windows OS environment, a UEM solution that gives you Admin level control over Windows Registry keys is a wise choice.
    2. Evaluate UX in the new environment. Once users are live in the new environment, monitor their UX with a third-party agnostic monitoring solution. If you assessed the legacy environment with the same UX solution you can indeed prove if you are/are not delivering a better desktop.

Jason E. Smith is the Product Director for Liquidware Labs

Photo credit: Anton Watman / Shutterstock

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.