Roger. The plot thickens. Then, you need to chase the pump discharge line end-to-end and figure out why. And as I recall, you said that would be difficult... Sounds like you don't have a high loop near the discharge point, or it's not vented and you're lucky enough to create a back-siphon scenario at +18 degrees of heel.
Probably too cold to do much checking, but plugging one end and blowing on the other will tell you if there is a vent or break in the line. Then, you could use water level to check for a high point. A go-pro aimed at the discharge while underway and heeling, so you could see what the water is doing at the thru hull (outside), might tell you if the velocity near the thru hull was forcing water in.
The discharge thru-hull isn't a forward facing scoop I assume?
Interesting problem. Thanks for posting.