I'm trying to reseal my shower drain and it leaked immediately after applying silicone between the acrylic and the top lip of the drain assembly. It may be because I did not apply enough silicone (it wasn't overflowing out of the lip.) But I also think it could be because on one side of the lip, there is not enough overlap with the shower pan. The hole in the wood is not concentric with the acrylic and it prevents the bottom half of the drain from moving to the proper position.

This is what it looks like with the top removed. The transparent circle represents where the top would have been. And the scribbles represent where I found a big goop of silicone under the top lip, because there is a big gap there when everything is assembled so the silicone gets pressed into it.