Tldr: The Windows build of Anki doesn’t support TLSv1.3.
I run my own sync server behind an Apache2 proxy for TLS termination, and I noticed while sharing that it wouldn’t work only on Windows devices.
After a couple of hours of searching and finally capturing the requests via Wireshark, I noticed that the TLS-handshake failed because TLSv1.2 wasn’t enabled on the server (only TLSv1.3). This wasn’t an issue on Linux and Android.
Enabling TLSv1.2 made it work for the Windows side as well.
IMO the Windows version of Anki should also support TLSv1.3 connections, restoring parity between the different platform-specific builds.
Thanks for looking at this report!