Princess 414 leaking in the rudder

Why are you pulling the rudder to seal the shaft?
Why not just adjust the packing? Looks like you have some room for adjustments.

If you must pull the shaft; That is a shaft key and usually just snug pressed into the shaft.
I use locking pliers (Vice-Grips) with a tight lock on the key and wiggle the key out. For stubborn keys, a tap or two on the pliers head, tapping away from the shaft pops it out.

I do hope your boat is on the land and not still in the water.

That key looks like it near end of life so get a new key. If that must be re-used, lightly file the key smooth to just remove any high spots that the pliers may have left on its surfaces.
Teflon grease on the shaft and re-install key.

So this is how Princess supports their rudders, on top of the stuffing box plunger. Looks like it works.
That key would be the safety factor I assume.

Please note the almost all around even wear on the tiller clamp bottom and the top of the plunger.
When your final adjustments are made, please ensure this even contact is replicated.
A little WP grease could help here also.
The components will last much longer.

The threaded rod is fixed. it should not twist. loosen the top lock nuts.
Tighten the remaining two nuts down the same amount of turn. I would just give 1/2 turn today.
clean up all and re assemble.
When the boat is back in the water is when to adjust them, just tight enough to stop the leaks but not to ad drag on the rudder moving.

This line is where the top plunger lowers into the packing box. You should see it change a bit while tightening down on the nuts.
Maybe clean this line with a brush and penetrating / cleaning oil-spray. This may help keep some more trash from getting dragged into the tube.



Not the nuts on the bottom of the threaded rod, but there may be nuts just under the ears of the top part. Loosen them, if present, a 1/2 turn also.

Please note this picture is less than 650 pixels.
Please submit your pictures less than 700 pixels.
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Wedge, Key, I'm sure other names.
As long as were looking at the same thing; Thingie protruding from the side of the shaft / post that slides into a groove on the tiller.

Now, I need to bring something else up;

How old could the gland material be inside the the gland assembly?
How long since it's last adjustment?
How bad was the leak?

Sometimes. sometimes, sometimes old flax just does not compress as it should and needs replacing.
This project is best done out of the water, like you are now.

Two years dry, no history before, I would replace all packing.

Did you try locking pliers (Vice Grips)?
It would be bronze quality. Same material as tiller and post.
A small and long punch and hammer my help if the punch can get a dent in the side of the key, tapping away (out) of the post.

Something like that, yes.
Shaft flax comes in different sizes and different materials.
Would you have the ships manuals you can get the correct size from?
Are you in a marina yard? Is there a marine tech available you help you?

Drop the Rudder in the yard and repack and then put all back .

standard maintenace

Are you in a marina yard? Is there a marine tech available you help you?