r/sysadmin•
ADynes

In Place Upgrades from 2019 -> 2022 / 2025 - Which services should and shouldn't do this?

Late last year we purchased all our Server 2025 licensing, Software Assurance, and CALs to upgrade everything. We started with a new server and a fresh 2025 install running only HyperV and Veeam and copied all the VM's over from the old server to the new server as is. We then repurposed the old server as a backup, installed a fresh copy of 2025 also only with HyperV and Veeam, then made replicas of all the server and set up a weekly replication.

Once that was in place we fresh installed all application servers, brought up new 2025 machines, got them running, turned off the old ones, waited a month, and deleted them. That took care of half our servers. I was then going to do the two domain controllers but with all the 2025 DC bugs I'm holding off.

With that said I now have a bunch of 2019 servers that I'm wondering if I can just in place upgrade: a SQL Server 2019 box, a File & Print server, and the two DC's all currently on Server 2019. Botht he SQL and the file server have a bunch of custom data pumps and stuff running on them which is why I really don't want to start fresh but I can. For the DC's I was thinking of doing them fresh and using Server 2022 then in place to 2025 once it's actually stable although I'd be happy with a in place on those also. We do have the refinements of Exchange 2016 that was offlined 6 months ago but I don't think that affects anything.

So what can "easily" be in place upgraded and what shouldn't be?

Posted Oct 14, 2025, 1:00 PM UTC

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