We purchased our new to us boat three years ago. At the time of the survey it was noticed that the rudder stuffing box was leaking water. No problem we thought. When got the boat to our marina we had it hauled at the yard close to us to get it repacked. At first it seemed okay but over time it started to leak again. We waited to the winter to have it stored and to address the leak. The yard told us that it looked like the stuffing box needed to be rebuilt. We had it done and hoped that was it. Recently took the boat out only to discover it still leaked. Doesn't leak when sitting in the slip, just under way. Called the yard up and talked to them about it. They tell me they had some older boats with the same problem, turns out the rudder post was pitted so bad the packing didn't work. Never heard of this but who knows. Unfortunately the yard we always used is closing down ( Tidewater in Baltimore ) I'm going to try tighening up the stuffing box a little more to see if that helps. Any input at this point would be welcomed.