[Klaatu]

I have a Catalina 22 Capri configured with the racing package. This includes bale that is mounted in a track on the front of the mast. When I tack and the jib switches sides occasionally the jib hangs up against the bale. I have attempted to raise the bale but still occasionally the jib hangs up. This is probably a simple problem to resolve but I am not the sharpest knife in the drawer.

 

[jrutledge33]

Capri 22 are nice boats! enjoy.
not sure how the headsail gets in between the forward lowers to hang up in here. it must be flapping a lot mid tack. are you holding the old leeward sheet until the headsail is ready to tack? try backwind'ing the headsail longer, until it's ready to come across.
also try lowering the car on the mast track to deck level when not in use.
or remove the car if you don't plan to use a spin or whisker pole.
FWIW

 

[Faster]

By your description it sounds like you're not flying the kite - if that's so then remove the fitting from the track for now. There may be a stopper of some sort that needs to be removed first to allow the car to slide off.

If you want to keep the bale there for when you'll need it, then some technique changes during tacks may be helpful. Try easing the sheet through the tack (after backwinding as suggested above) to prevent the soon-to-be-lazy sheet from flogging excessively. It may then not flail about enough to snag.