[klem]

What boat are you working aboard?

The preferred method for all of the schooners that I used to work with was to use cotton first, then oakum. On the hull, putty was dyed and then put into the seams after that. On deck, we poured hot pitch into the seams and then scraped the excess when it had cooled.

If things are coming out, you either used something inappropriate, the boat is working, or the caulking was not driven down deep enough in the first place.