Until Milhouse can play this position out, it really can’t be considered a real checkers program. Right now, even with an endgame database, it’s still clueless about how to proceed.
Addendum: Reinfeld’s How to Win at Checkers gives some details on winning positions like this. I recall reading it (my puzzle database includes puzzles from this book) but I’m unsure as to how to effectively merge the knowledge into my evaluation function. Still, worth looking at.