... Must issue a STARTTLS command first
Port: 25
Secure(SSL): No
Back to the Properties dialogue. On the Advanced tab, select This server requires a secure connection (SSL) and make sure the server port for outgoing mail is 587. Make sure also that you have selected My server requires authentication on the Servers tab.
Remove any unsent messages from the outbox, then close down Windows Live Mail and wait a few minutes for the program to complete its housekeeping and store the new SSL settings. Re-launch the program, then compose a new test message with a unique subject and send it to yourself. Post any new error message in your reply.