Perform an in-place upgrade of Windows Server 2016 VM to Windows Server 2019 VM

[DavidColey]

Hello - we are running a distributed 10.9.1 Enterprise deployment on VMWare, Windows Server 2016.  Our system admins think that they can perform an in-place upgrade of the OS on our VM servers to Windows Server 2019. 

Is that even possible?  According to them, nothing will change, no machine name changes, no DNS name changes.  They simply want to upgrade to the 2019 OS. 

@VinceAngelo , @George_Thompson , @JonathanQuinn  any of you ever run across this?

Thanks,

David

[DEWright_CA]

@DavidColey - We are just getting ready to do the same process at my locations. According to ESRI ProServices they don't have a issue with it being supported/unsupported as they say the support the OS vendors guidance.

But we are doing it in a staged manner; Web-Adaptor/IIS machines first, the AGS machines, then Portal with liberal VM backups and ESRI WebgisDR snapshots.

[DavidColey]

Huh, ok thanks @DEWright_CA .  Yes, that would be my approach as well, although I may have them start with the configuration server first, since it has no GIS components on it at all.  Then we have a Monitor server, upgrade, test.  Web Server, upgrade, test.  Portal > 4 AGS machines > 2 Datastore Machines > License Manager > finally the windows vm hosting our sql server . . .

[Scott_Tansley]

This intrigued me.  I was once told by a respected windows sysadmin that you couldn’t upgrade from 2016 to 2019.

 But it’s documented that you can:  https://docs.microsoft.com/en-us/windows-server/upgrade/upgrade-2016-to-2019

I’ve always used the opportunity to start with a fresh VM and a nice clean install of windows and then upgrade Esri as a part of that (from one machine to another):

https://enterprise.arcgis.com/en/portal/latest/administer/windows/migration-strategies.htm#ESRI_SECT...

so I’ve never done an over the top of windows server, but I have recently upgraded my windows 10 based dev environment to win 11 and it was seamless.

ultimately if you clone/snapshot each machine, then you have a rollback.  I like your approach of config server, webs server etc.

exciting times.  I’d be interested to hear how you get on?

[DavidColey]

sure thing @Scott_Tansley I'll post back anything we do, when we do.

[BillFox]

We followed a similar document for this on 10.7.0 to get from 2008R2 to 2012 to 2019 (Double-Hop) in 2020.

https://techcommunity.microsoft.com/t5/itops-talk-blog/how-to-in-place-upgrade-windows-server-2008-r...

Each hop to about 3 to 6 hours depending on the number of rounds of required Microsoft updates, reboots, network traffic, etc.

Everything worked fine.