I've been hit by this issue recently. On my configuration, print("a" * 10215) fails with an infinite loop of OSErrors (WinError 8). This even cannot by interrupted with Ctrl-C nor the exception can be catched.

- print("a" * 10214) is fine
- print("a" * 10215) is fine when preceeded by print("b" * 2701), but not when preceeded by print("b" * 2700)
- the problem (or at least with these numbers) occurs only when the code is saved in a script, and this is run by double-clicking the file (i.e. run by Windows ShellExecute I guess), not by "py test.py" or interactively.

My configuration is Python 3.7.3 64 bit on Windows Vista 64 bit. I wonder if anyone is able to reproduce this on their configuration.