Single Machine ArcGIS Server upgrading operating system

[JRHockersmith]

Have a single site (single machine) ArcGIS Server.  Used to serve cached tiles.  I upgraded ArcGIS Server to 10.9.1, then to 11.1.  I ran the server backup at each stage and have retained them.  I have a large direct storage device that holds the arcgisserver folder (with config-store and directories).

Now I want to upgrade the operating system on this machine.  How do I do this without creating issues?  My hope is that I can rebuild the operating system drive, install arcGIS Server, and then restore from backup. 

[AngusHooper1]

I have upgraded the underlying Windows Server OS of various ArcGIS Enterprise components without any issues. Take snapshots and test in your QA environment first but we had no issues (30+ virtual machines).

[DEWright_CA]

I agree with @AngusHooper1 , we did in-place upgrades for my entire platform (7 vms for DEV, 14 for STAGING, 18 for PRODUCTION) without issue. We went from Win2016 to 2019; will go to 2023 in the spring of next year.

Don't go through the whole wipe/rebuild if you REALLY don't need too...

[JRHockersmith · Accepted solution]

I needed to rebuild the operating system drive from scratch.

Conditions:

0. Simple Single Machine ArcGIS Server using only cached tile map servers.

1. arcgisserver folder (with config-store and directories) not on the c: drive.

2. I copied the machine.config.xml and config-store-configuration.xml from server\framework\etc and performed a backup using backup.py.

3. Rebuilt the OS.

4. Reinstalled ArcGIS Server.

5. Tried to restore using the restore.py.

     a. Prompted about SSL.  Selected Y to continue, failed.

     b. Didn't use restore.  In hindsight, I used port 6080 in the script.  Realized later that this version uses https at 6443.

6. Overwrote the config-store-configuration.xml with my backed up version.

7. Rebooted.

8. Wasn't able to use my maps that was referencing port 6080.

9. From ArcGIS Server manager, was able to view the maps.  The web browser launched at https://...:6443.

10. Used ArcGIS Server Administrator Manager to change the security/config to http only.

11.  Everything works.

12.  TODO: investigate using a portal and https.