This time I think I got it right. I came across a gasket material used for sound/heat insulation for engine rooms and hatches etc. They make various sizes and shapes including this small D shape:

I ran it all the way around the rim just below the top edge:

I followed this up by putting 3/4"w x 1/4" thickness weatherstipping from West Marine under the lip of the box itself:

I also filed off about 3/4" of the bottom of the corner that fits over the gutter/drain hole. No leaks into the bilges. Thanks to whoever it was on this site that posted the ideas. It just took me awhile to get it right.

I ran it all the way around the rim just below the top edge:

I followed this up by putting 3/4"w x 1/4" thickness weatherstipping from West Marine under the lip of the box itself:

I also filed off about 3/4" of the bottom of the corner that fits over the gutter/drain hole. No leaks into the bilges. Thanks to whoever it was on this site that posted the ideas. It just took me awhile to get it right.
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