rudder stuffing box leak

[Lady Ann]

Noticed water under the engine going down to the bilge. Traced it back to the rudder stuffing box. Seems it was going on for a while, I just got this box a few months ago. Can this be repacked in the water? Our should I just try tightening it down till a haul out? Any advice is appreciated,
Jason

[Della and Dave]

From what I understand, it's pretty normal for a new stuffing box to need to be tightened as the seals wear in.  Getting the right wrenches helps.  Nigel Caulder's book has a pretty good write up in it. I would defiantly try that first.  It might actually take two or three tries. With traditional stuffing boxes, a small leak is normal.  It's always possible that it is being caused by something like corrosion on the rudder post, but if it was out for the new box a couple of months ago, that shouldn't be the case.  It's also possible to get the packing in wrong, but that should have showed up as soon as you splashed if someone looked. 

As for changing it without a haul out, others here know more than me, but given the access issues, it seems pretty risky to me.  I have heard of going over the side and packing the outside with something to seal it, and then doing it, but that would be hard and more of an emergency thing to me. You would be under a lot of pressure to work fast, so it would be easy to leave a little old packing in or screw it up some other way.  I like the adage, you can have it quick, good or cheap, choose two out of three. 

[Sailorlou]

One of the things to be aware of is that rudder stuffing box leaks (at least in the 367 cutter) tend to drip onto the back side of the fuel tank and water collects between the rubber seal and the tank at the point that the tank sets on seal.  In salt water this will cause corrosion and eventually eat through the tank.  Especially the aluminium tanks. 
I know this from experience.  I have replaced two tanks in the eighteen years I have owned my boat.  The last tank I put in has six layers of tar epoxy coating it to keep it from corroding ever again and it is also bedded in Irish Cloth which tends to wick away water.  I also found that the factory did not do a good job in installing the original stuffing box.  It was finished rough and the flange did not seat properly.