I guess you are mainly complaining about when __exit__() implementation is built into the interpreter. E.g., given demo.py: with open("/dev/full", "wb") as file: file.write(b"data") print("All is well") print("Not executed") the output looks like All is well Traceback (most recent call last): File "demo.py", line 3, in <module> print("All is well") OSError: [Errno 28] No space left on device When __exit__() is implemented natively in Python, you get more of a hint: Traceback (most recent call last): File "demo.py", line 4, in <module> print("All is well") File "/home/proj/python/cpython/Lib/_pyio.py", line 457, in __exit__ self.close() File "/home/proj/python/cpython/Lib/_pyio.py", line 773, in close self.flush() File "/home/proj/python/cpython/Lib/_pyio.py", line 1210, in flush self._flush_unlocked() File "/home/proj/python/cpython/Lib/_pyio.py", line 1217, in _flush_unlocked n = self.raw.write(self._write_buf) File "/home/proj/python/cpython/Lib/_pyio.py", line 1614, in write return os.write(self._fd, b) OSError: [Errno 28] No space left on device Maybe another option would be to insert a virtual frame in the built-in version of the traceback: Traceback (most recent call last): File "demo.py", line 3, in <module> print("All is well") File "<built in>", line ???, in <context manager exit> OSError: [Errno 28] No space left on device