Mast shoe to compression post.. through bolt or not

[Eastward ho 24]

I replaced my compression post and I through bolted my mast boot right through into the compression post.. it leaked. I've got the mast off and going to remedy it . Before I messed with it the mast shoe was just screwed into the deck and a compression post was haphazardly stuck undr that. Needless to say it was wood, and wasn't tied to the keel so it rotted crushed and the roof came in a little bit. So I've got a new SS compression post tied into the keel and beat a few fiberglass shims in to get it back. I then through bolted the whole shabang ( the deck under the mast is solid fiberglass). Now I'm not sure if this will be a constant source of leaks or if I just did a shotty job ( I never ever seen to get watertight with ploysulfide and that's what I used I hate the stuff). So the mast is down I was thinking I'm gonna disassemble the whole thing and not sure if I ought to fill the through holes and then just screw the boot into the deck ( not going through) and screw the compression post up into the roof not going through? Seems that's the way to go but I'm looking for other avenues aswell

[RaymondR]

Put a hard rubber gasket under it.