How to convert Windows Server 2019 Datacenter Eval to Retail MSDN?

Question

I have bought the Visual Studio Professional Retail annual subscription for ~$2000 in Switzerland (would be $1200 in US) and claimed a key for Windows Server 2019 Datacenter - Retail. I do have an existing test installation of Windows Server 2019 Datacenter 180-day Trial/Eval and would like to activate it with this retail license, preferably without reinstalling everything. It's a single server, no domain controller role added or anything. In the UI the key doesn't work of course, but I also tried to remove the existing key with "slmgr /upk", installing the new key with "slui /ipk ABCDE-...", register with "slmgr /ato" and converting eval to retail with "dism /online /Set-Edition:ServerDatacenter /ProduktKey:ABCDE-... /AcceptEula". But always the dism command fails with error 1168. Should this work and is this documented somewhere? Could there be a language difference (installation is US-English and key is from my Swiss subscription) even though the MSDN downloads offer various languages (even English, but it's not clear if US-English is included). Or what else could be the problem? The dism log doesn't say anything special other than that it didn't work. In Visual Studio downloads there are two packs of "Windows Server 2019 Datacenter - Retail" keys with 5 keys to be claimed in each pack. Support told me they are identical, but just to be sure I'm mentioning this here too. Or could it be that the key is associated to a wrong update cycle (long-term, half-year, monthly)? I think all MSDN keys are the same, but I'm not sure.

Answer 1

Might also try using a kms key as intermediary step.
Dism /online /Set-Edition:ServerDataCenter /ProductKey:WMDGN-G9PQG-XVVXX-R3X43-63DFG /AcceptEula
https://learn.microsoft.com/en-us/windows-server/get-started/kmsclientkeys

then if successful use your own product key below after reboot
slmgr /ipk xxxxx-xxxxx-xxxxx-xxxxx-xxxxx
slmgr /ato

--please don't forget to Accept as answer if the reply is helpful--

Answer 2

Sounds like some on-off issue (kms error). I'd try to replicate it.

--please don't forget to Accept as answer if the reply is helpful--

Answer 3

I meant by clean install, but it sounds like it isn't necessary anyway based on your other thread.

--please don't forget to Accept as answer if the reply is helpful--

Answer 4

No, not at all. I was suggesting to clean install it to see if you can replicate the issue, but now seems a moot point. Why not just use the MSDN media and product key?

--please don't forget to Accept as answer if the reply is helpful--

Answer 5

Any way I could activate this through the command line

Yes, to do that you can
slmgr /ipk xxxxx-xxxxx-xxxxx-xxxxx-xxxxx
slmgr /ato

As to the conversion process the only supported method of converting an evaluation is to retail. What I posted was a work-around.
You can convert the evaluation version of Windows Server Standard to either Windows Server Standard (retail) or Datacenter (retail). Similarly, you can convert the evaluation version of Windows Server Datacenter to the retail version.
https://learn.microsoft.com/en-us/windows-server/get-started/supported-upgrade-paths#converting-a-current-evaluation-version-to-a-current-retail-version

--please don't forget to Accept as answer if the reply is helpful--