Kaatu - Leaks around deck hardware are a common problem. However, you should not try to fix the leak by plugging/filling/caulking the leak from the inside of the cabin. If you do, it is likely water will continue to leak in from the deck, but instead of making it's way into the cabin it will go into the wood core of the deck and cause rot. The proper fix is to remove the hardware and re-bed it on the deck using epoxy, 3M 5200 or some other equivalent sealing adhesive. Leave the hardware in the cabin unsealed so that if you develop a leak in the future you'll know about it and can fix it before it causes core rot.
Don Casey's book entitled "This Old Boat" provides detailed instructions and advice.
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