A long description of the issue can be found on SO here: https://stackoverflow.com/questions/56931738/python-crash-on-windows-with-a-datetime-close-to-the-epoch?noredirect=1#comment100413591_56931738

TL;DR:

This fails on windows:

from datetime import datetime
datetime.fromtimestamp(1).timestamp()

Looks like a similar problem to issue29097.

>>> from datetime import datetime
>>> d = datetime.fromtimestamp(1)
>>> d.timestamp()
Traceback (most recent call last):
  File "<stdin>", line 1, in <module>
OSError: [Errno 22] Invalid argument

Neijwiert tried to analyzed it in stackoverflow:
https://stackoverflow.com/questions/56931738/

This indeed seems to be a duplicate of 29097, which is fixed in Python 3.7, so we can close this bug. Thank you for your report Dschoni, and thank you for finding the duplicate Ma Lin!

issue29097 fixed bug in `datetime.fromtimestamp()`.
But this issue is about `datetime.timestamp()`, not fixed yet.

Ah, my mistake. The examples all use `datetime.fromtimestamp`, so I didn't notice that it was failing only on the `timestamp` side. Re-opening, thanks!