In place upgrading from Server 2019 to Server 2022 not working

[AdminLovesLEarning]

Chip Chip Chin Chin

When undertaking and in place upgrade from Server 2019 to Server 2022 it only allow s to keep nothing and undertake a fresh install. is there any prerequisites or is this feature not avlaible even though the documentation insinuates it can be undertaken. When ever i try it insist on a keep nothing clean install.

I'm using and evaluation ISO so could the be the issues? I wanted to upgrade then use a licence afterwards as there no licence option during the installation of server 2022.

 

[WindowsForum AI]

In-place upgrade from Server 2019 to Server 2022 is supported—but with some strict prerequisites. One key factor is that both the source and target must be of the same edition and installation type (for example, Standard to Standard, Datacenter to Datacenter, and matching between Desktop Experience or Core). Using evaluation media can be problematic because evaluation versions typically don’t support preserving your settings and applications during an upgrade.
Since you’re using an evaluation ISO, the installer recognizes it as such and will force a “keep nothing” clean install rather than retaining your configuration. The evaluation edition is designed for testing purposes and doesn’t provide the upgrade path that a fully licensed version would offer. If you intend to perform an in-place upgrade that retains your roles, settings, and data, you’ll need to convert your current evaluation to a fully licensed edition first—often done via the DISM command (for example, using a command like: DISM /Online /Set-Edition:ServerDatacenter /ProductKey:XXXXX-XXXXX-XXXXX-XXXXX-XXXXX /AcceptEula
Ensure you use the correct edition and key that matches your environment).
Once your current installation is in a production state, you should then be able to use an installation media that supports an in-place upgrade. This way, you can avoid the clean install scenario and migrate your settings and roles to Server 2022 as intended.
Hope that clears it up! Feel free to ask if you have more questions or need further clarification.

 

[AdminLovesLEarning]

converted and Windows 2022 DVD into an ISO then transferred to physical Hyper-V server and mounted. undertook in place upgrade and all options to keep all setting, etc present so hopefully this works. so far so good.
created a checkpoint and exported the VM in case of errors as a failsafe restore

fingers crossed

 

[WindowsForum AI]

Great to hear, Chip Chip Chin Chin! It looks like you've set up everything for a smooth in-place upgrade—converting the DVD to an ISO, mounting it on your physical Hyper-V server, and taking all the precautionary steps (checkpoint and VM export) as a backup are all excellent practices. Fingers crossed for a seamless transition, and do keep us posted on how it goes. If any issues pop up or you need further guidance during the process, we're here to help. Best of luck with the upgrade!
Cheers,
—ChatGPT