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Before you take any action you should know how your rudder & bearings are designed!

For sailing boats the two most used bearing designs are bronze or plastic bushings.
Bronze - a special kind of bronze, sometimes called bearing bronze as it has a "oily" feel - shall be regularly greased. There is usually a nipple somewhere for this. When it becomes old, the rudder easily wobbles when sailing.

Plastic -most often Delrin- is water lubricated. Shall not be greased - that could even harm the bushing. When getting old, the bushing swells due to increased water in the plastic. The swell results in a stiff rudder.

If a stiff rudder, and particularly with a delrin bushing, one should fix that ASAP! If unlucky the rudder may be impossible to dismount without destroying rudder and maybe areas around it (google and you will find).

Most likely you have to haul to inspect and fix the issue. To replace a (most often lower) bushing is more easy than one may think.

/J
 

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It is an easy operation, but not that easy. You have to haul the boat, the complete operation will take some few days:

1. Remove the rudder. Often easy. Maybe include some digging -that is then the worst part of all (I do not know how the rudder keel look). If there is a need for digging then you might position the boat over a hole or something where you can drop the rudder so no digging is needed.
2. remove the bushing. Sometimes it is glued with epoxy, Sikeflex or something - in that case use a chiesel. The old bushing is usually rather brittle so it will fall of in pieces.
3. Get a new bushing. Either buy a new standard bushing to your boat - I get the impression that there is a market for such - or have it made. For the latter case measure very accurately the rudder stock and the hole in the boat, and find someone who delivers rudder bushings.
4. install the new bushing. Many glue it with thickened epoxy, then it will not move around, and it work well together with the hull. And be tight as well!
(I have used epoxy, recommend that. See to that you do not get any epoxy on the inside of the bushing!).
5. re-install the rudder.

6. Launch and sail.

Part (3) could take some time, for posting or contacting someone who does the work. If you glue the bushing it will take some time for the glue to harden - let it harden really really.

Do not hurry with this job. Buy some beers instead, enjoy the work and sunshine - and beer.

Last time I did this it was winter, ground was frozen rock solid. Had to dig a 1 m deep hole. That was not fun.

/J
 
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