Anchor windless switch covers sealing

[Harry Harris]

Folks, I’m replacing my switch covers & rings on my ‘06 300 DA. There is no sealer between the ring & deck. I’m inclined to run silicone under the ring. Okay? Thanks for your advice. Happy Easter all.

 

[Harry Harris]

The pair of foot switches on the bow I mean. The lower ring isn’t bedded/caulked/sealed at all.

 

[techmitch]

Well, I’ve learned something already: that there is no d in winless!

Not sure where you learned that.
https://www.westmarine.com/anchor-windlasses
As for your sealing, in and around the screw holes should be sufficient.