Apologies for any initial ambiguity in the question, I will attempt to make it a little clearer.
I have published a map service in ArcGIS Server.
In publishing, I have specified this map service to be a cached map service (I have set the levels, cache location, tile format, etc. AGS has no problem with any of these settings).
The service publishes successfully and AGS tells me that I can monitor the creation of the cache through ArcCatalog.
When I go to ArcCatalog and check on the Cache Status it tells me that the cache generation is not in progress, (see screen grabs).
The AGS log files are telling me:
SEVERE Instance of the service 'System/CachingTools.GPServer' crashed. 2014-06-12T10:03:25 Server ‘Server Name’ 8252 11464 1
SEVERE Instance of service 'Service Name.MapServer' failed to process a request. AutomationException: Unspecified error 2014-06-12T10:03:24 Server Name 8001 3161900 17
SEVERE IPersistStream::Save failed. 2014-06-12T10:03:24 Service Name.MapServer
Has anyone else experienced this, and if so, have you figured out what the issue is?