> Will Python support a release for as long as it's supported by the enterprise version? For example, support for 1709 enterprise ends on 2020-04-14, so if we followed that, then Python 3.9 would require Windows 10 1803 or higher. That seems wrong while we're still supporting Windows 8.1, but what will the stance be when Python supports only Windows versions that use the modern lifecycle?

This needs a separate discussion on python-dev, but for issues like this I think it's fine to blame the underlying platform and recommend getting their updates. We don't have to work around every Windows bug for all time.

I'll read the rest of what's been happening on this issue when I'm less tired, but not quite up to it right now ;)