SMTP through Python - error, can't send mail

I'm unable to send mail via Python/Flask and the WebFaction SMTP. Settings I'm using are below:

MAIL_USERNAME =           os.getenv('MAIL_USERNAME',        'mailbox_username')
MAIL_PASSWORD =           os.getenv('MAIL_PASSWORD',        'mailbox_password')
MAIL_DEFAULT_SENDER =     os.getenv('MAIL_DEFAULT_SENDER',  'mail@1eyed.mwanstall.com')
MAIL_SERVER =             os.getenv('MAIL_SERVER',          'smtp.webfaction.com')
MAIL_PORT =           int(os.getenv('MAIL_PORT',            '587'))
MAIL_USE_SSL =        int(os.getenv('MAIL_USE_SSL',         True))

The error I'm getting back is "SendEmailError: SMTP Connection error: Check your MAIL_SERVER and MAIL_PORT settings."

I've tried using a MailBox I created as the username/password and I've tried using my webfaction account username/password and both result in the same.

What have I got wrong?

Edit: Updated with real FROM email - the error is still the same.

The error is raised via the Python socket library: socket.gaierror, socket.error

UPDATE: Turned on debugging and the exact error I'm getting is:

SSLError(1, u'[SSL: UNKNOWN_PROTOCOL] unknown protocol (_ssl.c:581)')