I had a grease gun once that did this - turned out that the spring pushing the rubber plunger down the tube was pretty shot and wasn't advancing the grease into the pump mechanism once it was about 3/4 of the way down the tube. The longer the spring gets, the less force it has. The hole in the middle was formed when the ram-rod was pushed in the retracted position...
Maybe try a new gun? I chucked the one above (think it was a Plews brand gun?) and replaced it with a LubriMatic which hasn't had this problem yet. I will admit I've not fully used up a tube yet.
I do have a gun at work that's refusing to push out the Mobil SHC I've got in it, probably time to see if the cartridge is empty or if that gun is shot too. (It came from McMaster-Carr or Grainger, I forget.)
later,
b