Blew rear freeze plug on 408

Yeah, silicon is pretty slick to be used on core plugs. I’d knock them all out, clean the bores and put them back in with weather strip adhesive or something similar.
I always used that tarry-looking dark brown permatex form a gasket(#2 (?)) in the short, white bottle with the brush built into the cap. It is excellent for water pump bolts and other bolts that thread into water jackets. When you loosen them to adjust a belt or something, you can tighten them right back up with no leaks.