Can't sign in with MSN versions 5 - 7 on Windows 2000

I made my own VM and after some wrangling with the root certificates, I managed to get the same error code you did.

This 80090326 code is SEC_E_ILLEGAL_MESSAGE, indicating an error establishing the SSL connection, unfortunately it’s pretty generic otherwise. I’m not surprised by this, due to the ciphers (more on this discussed in the Win98 thread). I tried using Wireshark to find out more but it just blue screens when I try to capture, tried a few versions too.

That said, any idea when this last worked? I suppose something could have changed on the server, but everything is still working on XP.