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Matthew McGlone

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Recommendation for upgrade path to Windows Server and SQL Server

I currently have several Windows 2008 R2 servers running SQL Server 2008.  i need to upgrade both. I was hoping to upgrade Windows to 2016 and SQL Server 2016.  But I'm not sure if I should do it side by side - building a Windows Server 2016 VM and installing SQL Server 2016 - then restoring a backed up database on the new server.  

Or the second option of doing an in-place upgrade to Windows Server 2016 and SQL Server 2016.  It should be noted that these are production servers.

Any recommendations?

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Scott Silva
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In place upgrades of critical servers just never seem to work perfectly again... Just like an airplane crash, sometimes you get lucky, but not often...
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Seth Simmons
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What's the frontend that SQL is serving? Is it compatible with the updated database version?

Go with Server 2019 if you can and a newer version of SQL.

If stuck on 2016 for both, then make sure both are up to date before restoring the .BAK file (backup) into the new SQL. It will update the existing database and stamp it with the new version.

Keep this in mind as that means no going back.

And, of course, make sure to back everything up before, during, and after. :)
I would build new VMs with the later version of Windows, load the later version of SQL, and then backup/restore the SQL data and point things over to the new server. That's the easiest way that gives you a way to go back in case something goes wrong.