Quarter Window Trim Sealing

I am installing the quarter window trim on my 1969. I used the same foam tape for the weatherstrip retainer on the extension pieces to hopefully provide a little better water seal.

Would it help keep water out appling some sealant/caulk at the transition where the hockey stick trim piece, the extension piece, and the drip rail overlap?

I have power windows and this looks like a leaky fit. Or am I just over thinking things?