This is what I get when I try to sign in on Windows 2000 now… I used to be able to sign in just recently and I haven’t changed anything at all to cause this that I can think of.
The reason for Win2k is because I’m on a Linux host and I can’t get MSN to work correctly in Wine so I use a VM.
If you haven’t looked it up already, the error message is ERROR_INTERNET_SECURITY_CHANNEL_ERROR. With that in mind I would start by heading over to Internet Options in the Control Panel or IE, Advanced tab, scroll down to the bottom and make sure that ‘Use TLS 1.0’ is on (assuming it’s there) and ‘Use SSL 2.0’ is off.
Note: I’m not 100% sure what you’ll see on Win2k and don’t have an install handy at the moment.