August 19, 2026 at 1:41 pm
Putting this here as we're currently on SQL Server 2019 installed on Windows Server 2019, all hosted as VMs in Azure. We've recently been handed down a directive to upgrade to Windows Server 2025 by the end of Sept (which, needless to say, is NOT going to happen by that time.)
My preference would be to stand up new VMs to replace the existing VMs, clean installation of SQL Server 2025, and migrate the databases to the new servers from backups. However, there's also some wrangling going on higher up in the organization that may nix the cost of having duplicate VMs, even if only for a couple weeks / a month, which would then put me on a collision course with an in-place OS upgrade. Lets leave out migrating the databases to Azure SQL / Managed Instance, as some of the databases use features not available in either of those (Filestream, linked servers to Oracle using Oracle Wallets,) so while that's the end goal (currently,) that's also not in the cards for this particular situation.
So what's everyones' thoughts on doing an in-place upgrade of an OS when it comes to SQL? Have you done it? Did it go smooth, or where there problems, or did it completely blow up? Am I worried over something small? Being VMs, we could snapshot the VM prior to doing an upgrade, I'm thinking ideally with the SQL services stopped (the snapshot also ONLY snaps the OS volume, SQL is installed to another drive on the VM with the databases on their own drive,) to minimize the number of parts in motion during the snap and upgrade, IF we / I go down the in-place route.
August 19, 2026 at 2:08 pm
Definitely use new VMs. Too many installation settings could matter here. The new VM approach also allows you to test with a db to two without having to wait for all dbs to be converted (assuming your instance holds multiple user dbs).
SQL DBA,SQL Server MVP(07, 08, 09) "It's a dog-eat-dog world, and I'm wearing Milk-Bone underwear." "Norm", on "Cheers". Also from "Cheers", from "Carla": "You need to know 3 things about Tortelli men: Tortelli men draw women like flies; Tortelli men treat women like flies; Tortelli men's brains are in their flies".
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