P=F/A
If you solve for F, then F=PA
The area of a .250 circle is only 0.049087385212341 square inches.
If the pressure is 100 psi, then actual force against the surface of the cup should be just under 5 lbs.
F = 100*0.049087385212341
F = 4.9 and change
What I don't know is what the pressure is to push the cup back out, likely not much, but in terms of hydraulic pressure, that does work in the thousands of PSI, the oil galleys aren't pushing that hard and have plenty of leaks enroute as pressure backs up