I had a particularly difficult issue to track down and finally discovered a solution. Sharing in case anyone has a similar issue.
I'm on 11.3 although I don't believe this issue is version specific. We use Field Maps and manage offline areas using custom basemaps. In the last few months, we lost the ability to create offline areas. It would just fail to create. Error logs would only say "Instance of the service 'System/CachingControllers.GPServer' crashed".
The error is related to OpenGL applications crashing when using VMware 12.5. The solution was to set a system environment variable and update the display adaptor version. Details can be found in the broadcom article Applications using VMware tools 12.5 is crashing
Once we implemented the resolution described in the broadcom article, everything began working again. Esri also has a technical support article Error: ArcGIS Server Print Service and Caching Controller Crash When VMWare 12.5 is Instal. Note, we did not have to implement one of the recommended solutions. Specifically, we did not do the following.
Hope this helps someone out there.
Same issue after upgrading from 12.4.5 to 12.5.3. Going to attempt to implement the solution on the windows server and see if I am able to get it working again.