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. Seeing the new build number tells you very little.
One more thing. After the upgrade, our patch tool still showed the old OS version, so patching stalled until it refreshed. Check that early.
SSM has to be online before anything else. It is the only way in. When it wasn't, the agent helped troubleshoot it first.
Still on 2016? What's your plan?
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