Windows Server 2016 reaches end of extended support on January 12, 2027. If you still run it on EC2, the clock is ticking.

I recently upgraded 10+ EC2 instances in place to Windows Server 2022. An agent did the pre and post validation, and a human approved every step. It saved us at least a few hours of checking. Also, every server got the same checks.

Testing taught me a few things.

First, pin the edition. A plain setup command stalled on the edition page, and SSM can't click a button. Now the agent detects the edition and a human confirms it.

Disk space was next. One test run failed because C: was too full. We grew the root volume from 30 GB to 50 GB. Today, 20 GB free is a hard gate. And never copy the media onto C:.

Know your rollback. Restoring an AMI gives you a new instance ID and IP. Replace Root Volume keeps both. So take a direct root snapshot before you start.

Go canary first. Upgrade one server, check it, then do the rest. Also, test the app and not only the OS.…