On one of my 16's I had a strange situation with mast leak when capsizing.
The mast alone, off the boat would float and dunk test caused no issues.
Only when the mast was raised and sails rigged did it cause a problem.
It would also retain the water and not leak when de-rigged after lowing the mast.
The mast was heavy and one could feel the water sloshing back and fourth while carrying, but it would not empty.
Required drilling a hole near base so as to empty it for transportation.
Resealed the mast head problem remained.
I then re-rivited and Sikaflexed the mast tang and the problem went away (I think)
So I concluded that the mast tang when under some tension (stays / main / Jib) was causing some movement to allow water in.