Can I upgrade Windows Server with Connection Server installed?

[hoon0715]

Hi all.

Connection Server is installed on Windows Server 2016.

And my customer wants to upgrade to Windows Server 2019. 

The easiest way is to install Windows Server 2019 and then reinstall Connection Server as well. 

However, after learning that it was possible to upgrade from 2016 to 2019, I thought about upgrading Windows Server 2016 with Connection Server to 2019. 

Is this really possible?

Has anyone done this, or does anyone know? 

Your answers will be of great help. 

Best regards.

[Hotrod76]

My recommendation would be to deploy a brand new 2019 server. While I don't think anything may happen during the OS upgrade process, you just don't know,  If the OS upgrade fails then you will have to redeploy the connection server anyway.  

[srietberg]

Im with Hotrod on this one. Couple of weeks ago we in-place upgraded a Windows Server to 2019. After some time we where experiencing some weird bugs regarding Windows Update, Server Manager, etc. So i would also recommend to deploy a new Server 2019 VM. Just because the Connection Server needs to be a reliable component in my opinion 🙂 

[hoon0715]

To. @Hotrod76 @srietberg 

I upgraded Winser 2016 with Connection server to Winser 2019 and Winser 2016 with AD/DNS/KMS server to Winser 2019 too.

Windows update will not work because it is a Private network.

It's still working without any problems.

I've made a clone of it to prepare for Error!

If something goes wrong, I'll leave a comment again.

Thank you for guys : )