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Follow the definitive Windows 10 migration checklist

Making the move to Windows 10 can be complicated unless IT follows some critical steps, including verifying application compatibility and training its users in the new OS.

Performing a desktop OS upgrade in the enterprise is rarely as simple as just inserting the installation media and running Windows Setup. Windows 10 migration is no exception.

Even though upgrading to Windows 10 tends to be a simpler process than some of the Windows OS upgrades from the past, there is usually a litany of tasks IT must accomplish before beginning an OS upgrade.

As a result, being methodical and working through this six-step Windows 10 migration checklist can help ensure a smooth upgrade process.

Perform a hardware inventory

The first box on the Windows 10 migration checklist to cross off is performing a hardware inventory. Some people might regard this step as unnecessary because any system that can run Windows 7 or Windows 8 should be able to run Windows 10. There is a difference, however, between a PC running Windows 7 or Windows 8 and a PC running either OS well. In some cases, aging hardware may run a legacy OS, but just barely. As a result, IT may find that some users can truly benefit from a PC refresh.

IT must make sure PCs have sufficient disk space for the new OS. If IT performs a clean install, it must verify that each PC has enough storage to accommodate Windows 10 and any applications. If IT performs an in-place upgrade, then it must make sure that users' PCs contain enough extra storage space to accommodate the upgrade process.

Verify application compatibility

Next on the Windows 10 migration checklist, IT must verify that the applications users work with throughout the organization work with Windows 10. Most applications that run on Windows 7 or Windows 8 will run on Windows 10, but there are exceptions. In some cases, applications may need shims -- which help old application program interfaces run on new OSes -- to run on Windows 10. In other cases, IT may need to get an updated version of an application before it will work on Windows 10.

Take care of licensing

Licensing is a really basic step on the Windows migration checklist, but it is important nonetheless. IT must ensure that it has purchased the proper number of Windows 10 licenses prior to the upgrade process. This is also a really good time for IT to perform an internal license audit and verify that it has the proper number of licenses for the applications users work with within the organization and that it has the required number of client access licenses for any servers or server applications the PCs will connect to.

Decide whether to perform a clean install or an in-place upgrade

IT professionals must pick between a clean installation of Windows 10, where they upgrade a system to the new OS completely from scratch, or an in-place upgrade, where they carry over programs, utilities, user preferences and more. Most of the time, a clean installation is preferable, but there are situations that warrant an in-place upgrade.

It is also important to make sure that anyone responsible for deploying or supporting Windows 10 receives proper training.

If IT performs an in-place upgrade, then it must make sure that Microsoft supports it. Microsoft puts restrictions on in-place upgrades. For example, IT cannot upgrade from a 32-bit OS to a 64-bit OS with an in-place upgrade. Likewise, there are Windows edition restrictions. For example, IT can't perform an in-place upgrade that takes a PC from Windows 7 Home Basic to Windows 10 Enterprise.

Train users and IT

Before IT moves forward with a Windows 10 upgrade, it must make sure that everyone receives proper training. For end users, training may be as simple as giving everyone a quick crash course in the finer points of the new interface.

It is also important to make sure that anyone responsible for deploying or supporting Windows 10 receives proper training. There are significant differences between Windows 10 and legacy Windows versions, so training for the IT staff is essential.

Prove your knowledge of the Windows 10 upgrade process and other features

Are you a Windows 10 expert? Flaunt your knowledge with this quiz about app compatibility, the OS upgrade process and more.

Perform a pilot deployment

Before IT upgrades the entire company, it should pick a few power users in each department and upgrade their PCs to Windows 10 as part of a pilot deployment. The pilot phase is a good chance to find and correct any unanticipated problems before performing widespread upgrades.

Next Steps

Windows 10 migration station

Three Windows 10 upgrade questions IT should ask

Is it better to stay with Windows 7?

This was last published in October 2017

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