What if you go Complete Job, will it continue caching? Also that area of interest feature class you've got there - "Governorate_WestBank". How much of the area is that covering? I notice when you do that, it doesn't update cache status percentage i.e. The percentage of completion is done for the full area, not just the area of interest, so it may have fully completed, even though it says 50% or whatever. Did you have a look at the map service to see what areas are/are not cached?
Hopefully that helps a bit 🙂