This was one of the easier projects I worked on this winter. Both port and starboard chainplates were leaking so it was pretty easy to remove them, clean them up, then reinstall. Once I removed the cover plates it was apparent why they leaked. There was no caulk between the chainplate and the deck from the top view. Someone, OK not just someone but the previous boat owner, had caulked the chainplates from the inside in an attempt to stop the leaks. It didn't work of course and only caused the water to linger longer in the deck area. Luckily, everything was solid when I did the inspection.

I used plenty of caulk when reinstalling the chainplates but only from the top. It is my philosophy that if something on the deck leaks into the cabin I would rather see the water drip down than be blocked by caulk from the cabin side. That is why I don't put caulk in the hole first and push the thing through. Just before the chainplate goes in the last inch or so I put a nice thick bead around it where it will meet the deck, then push it all the way in. If required, I add more caulk on the top. Finally screw the coverplate back in and wipe up any excess caulk. Done!

I didn't remove the aft chainplate, just the cover. I cleaned everything, caulked and reinstalled the cover plate. I also checked the bolts for tightness.

  Chainplate Photos
Starboard chainplate has one screw that is larger
Not too much caulk, no wonder they leaked
Clean vs. original chainplate
Some discoloration due to leaking but wood is solid
Chainplate reinstalled
No caulk on inside so that if it leaks it will be visible and not soak into the deck
Slight gap between bulkhead and plate. Bulkheads may not be original equipment
Aft chainplate before cleaning
Cleaned and caulked