I can confirm this bug in Python 2.6 on Ubuntu 9.04.

>>> server = smtplib.SMTP('smtp.gmail.com',587)
>>> server.helo()
(250, 'mx.google.com at your service')
>>> server = smtplib.SMTP_SSL('smtp.gmail.com',465)
>>> server.helo()
Traceback (most recent call last):
  File "<stdin>", line 1, in <module>
  File "/usr/lib/python2.6/smtplib.py", line 371, in helo
    self.putcmd("helo", name or self.local_hostname)
  File "/usr/lib/python2.6/smtplib.py", line 318, in putcmd
    self.send(str)
  File "/usr/lib/python2.6/smtplib.py", line 310, in send
    raise SMTPServerDisconnected('please run connect() first')
smtplib.SMTPServerDisconnected: please run connect() first


** Changed in: python2.6 (Ubuntu)
       Status: New => Confirmed

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smtplib.SMTP_SSL is broken
https://bugs.launchpad.net/bugs/378494
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