Just reporting this here since there doesn't seem to be anywhere else:

If the first crossing at Three Island Crossing is deep enough to caulk the wagon and float it across (and you do so successfully), and the second crossing is shallow enough to ford, the game incorrectly gives you a 0% chance of success when fording the second crossing, and a high chance of success when caulking and floating. This isn't just a display bug, since caulking and floating will work, when the wagon should always crash.

Note: I encountered this in today's Pandemonium contract.