Work day: MDT (part 1)

At my day job, I’ve been tasked to upgrade or migrate all of our Windows 7 machines to Windows 10. I’ve been working at this task for just over three months, and we’re about a third of the way complete with targeted completion at the end of March of this year. This is part 1 of a series of posts in which I’ll describe the process of configuring a server with Microsoft Deployment Toolkit and Windows Deployment Services to complete this task.

In completing this task I had the following aims:

  • Require minimal effort to actually run the upgrade at each client
  • Preserve all user data on each client
  • Preserve installed applications where possible
  • Require minimal effort to reconfigure applications on each client after the upgrade

Part 1: Configure MDT for an in-place upgrade

Reference: https://docs.microsoft.com/en-us/windows/deployment/upgrade/upgrade-to-windows-10-with-the-microsoft-deployment-toolkit

I found that there was already a server in the environment running Windows Server 2012, with the Microsoft Deployment Toolkit and Windows Deployment Services installed. The organization had been using it to apply a Windows 7 SP1 image to new machines, and it was reasonably up to date. After some brief research, I found the article linked above and confirmed that direct upgrade from the organization’s existing computers from Windows 7 to Windows 10 should be possible. From there, since the deployment share already existed I was able to add the version of Windows 10 I wanted to deploy, create a task sequence, and successfully test the upgrade process on a client computer without any real issues.

Some nuances that aren’t captured in the Microsoft document above:

  • If you obtain your Windows 10 image from the Volume License Service Center, you may find that your ISO actually contains .wim files for a number of different SKUs, and you need to specify which one you’re using in your Task Sequence
All of the above .wim files were in one ISO I obtained for Windows 10 Pro
  • When selecting my ISO, I elected to take the next-to-most current version available. My users don’t need to be on the cutting edge in terms of new features (if they did, they wouldn’t still be running Windows 7), and the most recent version tends to be where Microsoft is still fixing bugs, so it’s safer to stay one step behind

All of this looks pretty straightforward, right? You’d think so. I ran into a few hiccups along the way though, so stay tuned for the rest of this series!

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