Note, that we have a regression in 3.8. There is a use case for "break" in "finally", and such code is even used in the stdlib. And who know in what third-party code it is used. In specific circumstances (see msg349513) it now can cause a crash. Other example: import contextlib def simple(): with contextlib.nullcontext(): for number in range(2): try: return number finally: break simple() It just raise an exception in 3.8, not crash: Traceback (most recent call last): File "<stdin>", line 1, in <module> File "<stdin>", line 7, in simple TypeError: 'range_iterator' object is not callable