Outlook: Unable to Configure Outgoing Email Server with Secure Connection

When configuring Outlook to send email via SMTP with a secure connection, the operation fails.

In particular, when using the “Use same settings as my incoming mail server” option, the account test succeeds when testing the POP account, but fails using the SMTP account. Thus the password supplied for the POP account is confirmed as being correct.

This may occur if the password has a question mark (?) in it. Change the password.