Hey Aljo, I noticed something going back through some saves that might help your team reproduce and potentially fix this bug- in every single case, on multiple players, right before the resign period (like on the day the auto sign happens that I spoke about above) a conversation with the coach pops up when you've won the Conn Smythe. On a new playthrough I simmed all the way to the contract period without winning the Stanley cup and Conn Smythe that year, and every time I got the contract signing options. It might be coincidence because I didn't rigorously test this, but it seems like there might be a connection to look at there. Hope that helps!