I test builds using a Windows VM. It's often off for weeks at a time. When I boot up, the time is usually stale and any HTTPS/TLS request won't work (by TLS design).

However, the Windows "Set Time Automatically" feature never works for me, no matter how often I toggle it.

Today I had a hunch: "Set Time Automatically" calls a server over TLS, so also doesn't work if the time is incorrect. To check I set the time to a few minutes off: close enough for HTTPS to work, but still incorrect. Sure enough, "Set Time Automatically" immediately worked. Not sure if it's NTS over TLS, or DNS over TLS, but it's breaking somewhere.

Did MSFT really implement a "Set Time Automatically" feature that requires the time to be correct to function?