Migration from Windows 2008 R2 to Windows 2016

[MichaelSchoelen]

Currently our IT shop is migrating data centers. Our current data center (C1) has all machines running Window Server 2008 R2, and the new center (C2) has all machines running Windows Server 2016. Soon, we will have to migrate our ArcGIS Enterprise from one center to another. Which of these (if any) methods is best?

1. Have them set up the 2016 server images at (C2). We will install the software. Then using the join machine migration method, we link the machines together, then unlink the original (C1) machine. 
   Concern: Can you join a 2008 R2 machine with a 2016 machine? I've seen 2012 and 2016 machines joined before.
   
   
2. Run the windows upgrade on the original machine (C1). Then our data center team, using VM tools, can clone it in-state to the new data center (C2). 
   Concern: Upgrading OS from 2008 R2 to 2016 is a big jump. I'm concerned that this upgrade will break ArcGIS.
   
   
3. Have them set up the 2016 server images at (C2). We will install the software. Then using WEBGISDR, we will migrate all of the content.
   Concern: Can you use WEBGISDR between a 2008 R2 machine to a 2016 machine, even if the configurations are identical?

[BillFox · Accepted solution]

Hi Michael,

Choose curtain number 1

[JonathanQuinn]

I concur with Bill Fox‌, I'd go with Option 1. Option 3 is good if you want to validate whether your new environment is working prior to switching over, but requires knowledge of etc\hosts file changes and there's a risk of some data loss as people can still create content on your first environment while the second is restored/validated, before you switch over.