I have a Windows Server 2008 guest on Windows 7. I can receive emails from all my accounts. I can send email from all of my accounts EXCEPT my bluehost account (personal email). Can't connect to the smtp server. "The message could not be sent because the connection to smtp server box475.bluehost.com timed out".
Of course, this woks fine from the host. If it were a password issue, I would be asked for a new password.
Incidentally, I am using Thunderbird in all cases.