First off what gun do you have. I guess that it is a caswell. Either way you need only use around 7 to 12 lbs of air at the gun. You will also need an air dryer to catch any moister in the air line. It sounds like you regulator isn't doing it's job. Your gun shouldn't even know about the pressure behind the regulator.
You might try putting a big regulator at the pump, so you can regulate it there as well.
Also DO NOT fill your cup full. only fill it about half at the most.



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