Prindle 19 rudder system
There is a small hole below the V jam on the arm. This is where the line that pulls your rudder down should be lead. You'll have to re-feed this line from where it leaves the rudder casting and enters the arm. Taping this line to a coathanger will help you to feed it through the arm. It should have a stopper ball at its' end.

Check the pdf file from the manual. The pull down line has a ball and exits through a hole at the end of the tiller arm. The pull up line has the aluminum tube and exits through the v cleat on top of the tiller arm.
Check the sheaves in the system are not stuck and roll.
I tried those safety pins several years back. The starboard one fell out while sailing in about 15+ knots of breeze. The pintle fell down several inches causing the rudder casting to flop over 45 degrees and chip the gelcoat. It wasn't easy getting it together and back to shore. Since then I use a split ring with a curved end that makes it easy to attach and remove. I haven't had a problen in 10 years.
The circular plastic shims work well. Murray's marine sells them. I'm not sure if Catsailor does. For recreational sailing I loosen the bolt where the rudder pivots slightly. This makes it easy to raise and lower. For a race I'll snug it up so that the rudder just barely falls under its' own weight while sitting on the beach. This makes it harder to raise and lower but it takes a lot of the slop out and improves helm response.
Thanks, I will try split rings. I have almost the identical story to yours... What about using a cotter pin?
Matt
I used cotter pins when I had a P16 because there isn't much room to insert a split ring. A cotter pin would be fine for your use. I take my rudders off when I trailer the boat to races or when there is unusually nasty weather on the way when my boat is on the beach. I really don't like this type of rudder system. I've learned how to tweak it after all these years but would prefer any of the other systems available.
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