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How to In-Place Upgrade Windows Server 2008 R2 to Windows Server 2019

thomasmaurer's avatar
thomasmaurer
Icon for Microsoft rankMicrosoft
Jul 23, 2019
As you know the Windows Server 2008 and Windows Server 2008 R2 are out of support on January 14th, 2020. Customer will need to upgrade their Windows Server 2008 and Windows Server 2008 R2 to a newer ...
Windows Server Upgrade Paths Diagram.png
Updated Jul 13, 2025
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life777eternal's avatar
life777eternal
Copper Contributor
Jan 27, 2025

Greetings thomasmaurer, thank you for sharing this information. I have upgraded my Windows Server 2008 R2, to Windows Server 2012 R2 Standard, and now that I have the Windows Server 2019 setup running, it shows that I can't upgrade and keep the installed apps and files. (have an online backup too, on another server, though an upgrade is preferable).  Also I noticed that one of your screenshots has Datacenter on it. Would I have to upgrade the Server 2012 R2 Standard to the "Datacenter" edition first? The upgrade was successful, running 6.3.9600 N/A Build 9600. It's running on an Ubuntu Linux VPS. … and aye, I already noticed that IIS did not survive the upgrade, and my server website is not working now, which is needed for my HalcyonGrid. https://github.com/HalcyonGrid

 

 

Thank you, Shalom.

 

Also this kept appearing, and I didn't write any HTML here, I just added hyperlinks.