This might be considered a bug in smtplib but a simple 2 line workaround can be added to mailer.py in the mean time.

In the "smtpTest.py" file (it's attached) the "works" function uses the ehlo() fuction to refresh that data before attempting to send starttls() or login().  

when using tls with gmail (and perhaps other smtp servers) the available features changes after you send starttls.  However the esmtp_features dictionary of the connection doesn't update when you send starttls.

The fix I made in Roundup\mailer.py was to add a call to self.ehlo() in the SMTPConnection.__init__ function just before both self.starttls() and self.login()

-Trevor D