Having to jump well pump to get water. Full 240at pressure switch.

Old school pressure switch, no reset bar. Newish breaker and pressure switch.

It was pumping fine, then nothing. I have 120v at both power wire on the pressure switch. However, if I disconnect the two power wires and jump the switch from my generator using some 220 wire, the pump works. Am I somehow not getting enough amps from my pole? Any advice?