If you're getting air out of the tap, then for sure you have a leak on the passive side of the pressure pump.

I don't know about your fittings though Craig. It may be tough to find a fitting that's pulling air. Maybe if you keep them dry enough with a good light you may see them weeping a little when the pump isn't pulling.

They may reseal upon further tightening, and they may not and you'll have to replace a fitting or two.