Do you have water entering bilge via keel bolts?
This could be galvanic interference between keel fin and keel plate/bolts.
To be sure i would lower the keel (turn the keel bolts open from inside).
Then remove all caulking on top of your keel fin and caulk excessively with new silkaflex.
Pull keel fin up (tighten keel bolts equally from inside bilge).
Now is sure watertight again!
Then paint it again.
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