I did some messing around, and it appears that after you pass the normal level, the number doesn't update automatically in the stack inserter.
That being said, there's not really a ton I can do, other than say just check and uncheck the Override Stack Size Box, it will then update.
I will mention this to the devs.
Update: I have made a forum post under the bugs section. Just have to wait to see if it gets a response.