Mail (OS 10.7.5) does not sent email (ports: 25, 465, 587) with firewall set to high.
Downgraded OS to 10.7.5 having problems with Mail (unable to search or see archive in 10.9). Worked with four senior advisors and came empty handed.
Problem appears in Mail not supporting the default SMTP ports. Apparently Apple's SMTP server does not recognize credentials via SSL...
Modem (SBG6580 and SBG901) with forwarding docs to include port 587 (not listed as supported by firewall set to high).
Only gmail accout appears to sent messages. Outlook account failed as well.