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Upgrade Engine and OS

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Hi all,

I have several servers running : Windows Server 2008 R2 OS + SQL Server 2008 R2 , Express and Standard Edition.
Now I want to in-place upgrade these servers cause End of Mainstream support.
I have prepare SQL Server 2012 , 2014 , 2016 Standard Edition license and Windows Server 2012 R2 , 2016 OS license.
What latest version I can upgrade my server ? Should I upgrade OS first then SQL Server or vice versa ?

I assume steps:

- Backup all databases.
- Insert Windows Server OS cd into my servers, run setup.exe to upgrade OS version first.
- Run new SQL server setup file , choose upgrade.

Please give me some advice or document, thank you very much.


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