I'm looking for advice on upgrading my Windows 11 21H2 Azure virtual machine, which is currently out of support. My goal is to upgrade to version 23H2 or 24H2 while keeping all my apps and data intact. However, Windows Update isn't providing the upgrade option. I'm considering a few approaches: mounting the ISO and running setup.exe, using the Windows Installation Assistant, or, as a last resort, performing a clean install. I'd love to hear from anyone who has upgraded VMs before—what method worked best for you? Did you face any driver or compatibility issues? Also, did you have to handle TPM or Secure Boot checks? What potential pitfalls should I be aware of before starting this upgrade? Any tips would be greatly appreciated, especially if you manage multiple VMs in a professional setting!
5 Answers
Make absolutely sure you have backups before trying to upgrade! If something goes wrong, roll back and reassess your strategy. If you're managing a CRM or similar critical system, it might be worth trying the upgrade, but more often than not, a clean start with a new VM is the way to go.
Good call! Having that backup will save you a lot of headache.
Skipping compatibility checks can make in-place upgrades easier. I’ve had success with this approach—just make sure you use the Media Creation Tool when the Update won’t cooperate. It's smoother than you might think, although the usual precautions apply.
Just a reminder though, in-place upgrades often leave systems messy. I’ve seen so many cases where it leads to more trouble. Just something to keep in mind!
Exactly! That's why I always encourage having a backup plan.
Have you tried applying the latest updates manually? Just because your version is out of support doesn’t mean you can’t check for updates—I've updated VMs successfully, even on older versions. If that's not working, consider cleaning out the SoftwareDistribution folder and restarting to see if that helps.
Honestly, just create a new VM and migrate your applications there. Upgrading in-place can be risky, and cloud solutions generally favor spinning up new instances instead. Windows upgrades can often lead to problems down the line.
Creating a new VM and migrating your services is the best practice. In-place upgrades might seem appealing, but I’ve seen too many issues arise from them. It’s worth the extra effort to start fresh.
Definitely back everything up! You might want to copy the ISO files to a local folder and then run the upgrade from there.