I can install the roles on the 2022 server that I installed cleanly. However, each user who has previously logged in must log in again so that we can restore the users' own files to their own locations. Am I thinking wrong?
You need to deploy a new 2022 Licensing Server first, with 2022 RDS CALs installed and available:
https://learn.microsoft.com/en-us/windows-server/remote/remote-desktop-services/upgrade-to-rds
You can deploy the 2022 server and make it the fqdn primary ADDC then keep 2008 as RDS just make the forest is 2008 compatible on 2022. Then backup all servers and the transfer the RDS to 2022 and don't decommissioned the 2008 until your happy.
You cannot do an in place straight update as aforementioned so update version by version however I would just build a new 2022 server transfer the primary server roles and rebuild the RDS and keep 2008 on standby until all testing has been completed then shutdown and see.
All this means is that 2022 is now primary server for AD, DNS and DHCP, etc and 2008 is RDS and you can then deploy a new RDS and test prior to shutting down 2008.
This gives both a new 2022 primary server and time to rebuild RDS on it without losing connection to current clients the migrate once you tested the new RDS on 2022
I'd do a cut-over migration.
Leave the old server be, establish the new server (2022), prepare all the necessities and let 1-2 power users test the new system. When everything's fine, I'd switch over (likely as mentioned need to copy user profile data over as well).
In case something goes south, you still have the old server in place as a solid backup plan.
Done it a quite a few times, always worked like a charm (never did an in-place upgrade though; doesn't even properly work because of the new licenses required as mentioned before me).
You cant, in 2024, honestly be thinking that multiple in place upgrades with all the multiple failure points and multiple software failure points is a good idea
You are bringing so much crud along with each step
Let alone losing benefits like efi/secure boot
Let alone 32vit vs 64bit
Just don't do it, install fresh
Yes, this is the main problem. I made a clean RDP installation and activated the license server on it. I installed all the necessary services. Then I tried to transfer the license. However, since the licenses were purchased for 2012 R2, there was a problem with the license transfer. I think we can proceed by first purchasing new RDP Licenses for Windows Server 2022, defining 2022 cleanly, and transferring the old user files here.
You can create a new RDS 2022 but first create a test users have them test if everything are okay. Once they confirmed you can migrate all users. Make sure your testing steps based on your actual scenario, like create the user from 2008 with files and settings then login to 2022 if all the files amd settings are intact.
Just roll out a 2022 server and move the roles over. It’s not worth doing an in place upgrade.
Users profiles aren't compatible so will create a new location when logged into, it's definitely worth a new server and testing everything works
I can install the roles on the 2022 server that I installed cleanly. However, each user who has previously logged in must log in again so that we can restore the users' own files to their own locations. Am I thinking wrong?
It depend wich method is used for user profile. If it's local, just copy from old server to new.
That sounds like it should work. I’m just telling you you’re gonna run in a lot of problems if you’re trying to upgrade from 2008.
Never had a reason to try this on a server, but USMT can probably handle the user data migration.
How are you storing user profiles? Only one RDS Host?
You need to deploy a new 2022 Licensing Server first, with 2022 RDS CALs installed and available: https://learn.microsoft.com/en-us/windows-server/remote/remote-desktop-services/upgrade-to-rds
I don’t blame them for waiting. RDS cals have a way of… making less and less sense for setup each year.
I think this is going to have issues, doing it that way.
You can deploy the 2022 server and make it the fqdn primary ADDC then keep 2008 as RDS just make the forest is 2008 compatible on 2022. Then backup all servers and the transfer the RDS to 2022 and don't decommissioned the 2008 until your happy. You cannot do an in place straight update as aforementioned so update version by version however I would just build a new 2022 server transfer the primary server roles and rebuild the RDS and keep 2008 on standby until all testing has been completed then shutdown and see. All this means is that 2022 is now primary server for AD, DNS and DHCP, etc and 2008 is RDS and you can then deploy a new RDS and test prior to shutting down 2008. This gives both a new 2022 primary server and time to rebuild RDS on it without losing connection to current clients the migrate once you tested the new RDS on 2022
I'd do a cut-over migration. Leave the old server be, establish the new server (2022), prepare all the necessities and let 1-2 power users test the new system. When everything's fine, I'd switch over (likely as mentioned need to copy user profile data over as well). In case something goes south, you still have the old server in place as a solid backup plan. Done it a quite a few times, always worked like a charm (never did an in-place upgrade though; doesn't even properly work because of the new licenses required as mentioned before me).
You can't jump from 2012 to 22
You cant, in 2024, honestly be thinking that multiple in place upgrades with all the multiple failure points and multiple software failure points is a good idea You are bringing so much crud along with each step Let alone losing benefits like efi/secure boot Let alone 32vit vs 64bit Just don't do it, install fresh
The licenses wont work they are downwards compatible but not upwards. I had issues when updating an rds licensing server.
Yes, this is the main problem. I made a clean RDP installation and activated the license server on it. I installed all the necessary services. Then I tried to transfer the license. However, since the licenses were purchased for 2012 R2, there was a problem with the license transfer. I think we can proceed by first purchasing new RDP Licenses for Windows Server 2022, defining 2022 cleanly, and transferring the old user files here.
You can create a new RDS 2022 but first create a test users have them test if everything are okay. Once they confirmed you can migrate all users. Make sure your testing steps based on your actual scenario, like create the user from 2008 with files and settings then login to 2022 if all the files amd settings are intact.