Remote Desktop Services Upgrade from Windows Server 2012 R2 to 2016

Question

Hi,

Currently, we have our remote desktop services on Windows server 2012 R2 and would like to upgrade them to windows server 2016 Datacenter.

We have
1 Win server 2012 R2 with Broker Role
2 Win servers 2012 R2 with RD Web, Gateway, and License Roles
15 Win servers 2012 R2 with RDSH Role

All these servers are in production.

1. I went through the article below and it suggests server upgrade flow. Since we are in production where our customers use it to access our application and I want to get your guidence. My worry is that by performing windows upgrade to 2016 Datacenter will it make changes to Registry or IIS setting or anything that I need to aware of. Or after upgrading all the built in RemoteApp will work just fine. for example., calculator, rdp. https://learn.microsoft.com/en-us/windows-server/remote/remote-desktop-services/upgrade-to-rds
2. Can I have another RDS deployment in 2016 by spinning up the new windows server 2016 side by side without touching the current RDS deployment where I can test RDS 2016 with our application?. If so do I need to have a new RDS license during this period or can I use an evaluation license?

Please suggest.

Thanks a lot.

Answer 1

Hi,
1.From the migration part of document, it highlighted that there is no direct in-place migration from RDS in Windows Server 2012 R2 to Windows Server 2016 but instead for most of the RDS components, you first upgrade to Windows Server 2016 and then migrate data and licenses.
The only components with a direct migration are RD Web, RD Gateway, and the licensing server.

So if you want to keep current settings of RDS 2012, you need to upgrade components like RDCB and RDSH to server 2016 and capable to migrate other components to server 2016 directly.

2.You could also build another complete RDS deployment with Server 2016 and utilize Grace Period for testing or pilot purpose. But this brand new RDS deployment will not inherit any existing configuration of RDS 2012 and need RDS CAL 2016 when users remoting to RDSH 2016.

Reference links:
RDS and TS CAL Interoperability Matrix

https://social.technet.microsoft.com/wiki/contents/articles/14988.rds-and-ts-cal-interoperability-matrix.aspx

Migrate your Remote Desktop Services deployment to Windows Server 2016

https://learn.microsoft.com/en-us/windows-server/remote/remote-desktop-services/migrate-rds-role-services#migrate-session-collections

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Hope this helps and please help to accept as Answer if the response is useful.

Thanks,
Jenny

Answer 2

I'd verify system and servicing health by running;
sfc /scannow

also system update readiness tool
https://learn.microsoft.com/en-us/troubleshoot/windows-server/deployment/fix-windows-update-errors

Then check for errors in;
%SYSTEMROOT%\Logs\CBS\CheckSUR.log

--please don't forget to Accept as answer if the reply is helpful--