Stack size was fairly recently updated to allow for stacks of more than 255. It's possible something was missed, so if you had a stack over that size and whatever wasn't updated happens you'd end up with the old stack size mod 256. So, if you had 500 you'd end up with 244, and if you had 1000 you'd end up with 232.
If you limited yourself to stacks of 255 or less you wouldn't have any issues. If you're looking to track it down you'd need to find everywhere that the stacksize is assigned to a variable or passed into a function and make sure none of those places is using an unsigned char instead of a uint16.
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