Roundup, smtplib, TLS and MS Exchange

[carlistixx]

Hi,

I'm using the roundup issue tracker (http://roundup.sourceforge.net)
which uses smtplib to send mail. It all worked until we moved to a
hosted Exchange MTA. The hosting provider requires the use of TLS. Now
roundup can't send mail.

My version of python is:
Python 2.3.4 (#1, Feb  6 2006, 10:38:46)
[GCC 3.4.5 20051201 (Red Hat 3.4.5-2)] on linux2

Roundup version:
$ roundup-server --version
1.1.2 (python 2.3.4)

I've reproduced the SMTP conversation below. I'm not sure if it's a
problem with Roundup, smtplib, or Exchange.

Any assistance appreciated.

[foobar at moe tracker]$ roundup-server -p 8081
roundup=/home/foobar/roundup/tracker
Roundup server started on :8081
send: 'STARTTLS\r\n'
reply: '503 5.5.2 Send hello first\r\n'
reply: retcode (503); Msg: 5.5.2 Send hello first
send: 'ehlo moe.foobar.local\r\n'
reply: '250-smtpx15.msoutlookonline.net Hello [202.173.131.223]\r\n'
reply: '250-SIZE 31457280\r\n'
reply: '250-PIPELINING\r\n'
reply: '250-ENHANCEDSTATUSCODES\r\n'
reply: '250-STARTTLS\r\n'
reply: '250-AUTH LOGIN\r\n'
reply: '250-8BITMIME\r\n'
reply: '250-BINARYMIME\r\n'
reply: '250 CHUNKING\r\n'
reply: retcode (250); Msg: smtpx15.msoutlookonline.net Hello [202.173.131.223]
SIZE 31457280
PIPELINING
ENHANCEDSTATUSCODES
STARTTLS
AUTH LOGIN
8BITMIME
BINARYMIME
CHUNKING
send: 'AUTH LOGIN ************==\r\n'
reply: '334 ************\r\n'
reply: retcode (334); Msg: ************
send: '************\r\n'
reply: '235 2.7.0 Authentication successful\r\n'
reply: retcode (235); Msg: 2.7.0 Authentication successful
send: 'mail FROM:<user at domain.com> size=1090\r\n'
reply: '451 5.7.3 Must issue a STARTTLS command first\r\n'
reply: retcode (451); Msg: 5.7.3 Must issue a STARTTLS command first
send: 'rset\r\n'
send: 'STARTTLS\r\n'
reply: '503 5.5.2 Send hello first\r\n'
reply: retcode (503); Msg: 5.5.2 Send hello first
send: 'ehlo moe.foobar.local\r\n'
reply: '250-smtpx15.msoutlookonline.net Hello [202.173.131.223]\r\n'
reply: '250-SIZE 31457280\r\n'
reply: '250-PIPELINING\r\n'
reply: '250-ENHANCEDSTATUSCODES\r\n'
reply: '250-STARTTLS\r\n'
reply: '250-AUTH LOGIN\r\n'
reply: '250-8BITMIME\r\n'
reply: '250-BINARYMIME\r\n'
reply: '250 CHUNKING\r\n'
reply: retcode (250); Msg: smtpx15.msoutlookonline.net Hello [202.173.131.223]
SIZE 31457280
PIPELINING
ENHANCEDSTATUSCODES
STARTTLS
AUTH LOGIN
8BITMIME
BINARYMIME
CHUNKING
send: 'AUTH LOGIN ******************************==\r\n'
reply: '334 ************\r\n'
reply: retcode (334); Msg: ************
send: '************\r\n'
reply: '235 2.7.0 Authentication successful\r\n'
reply: retcode (235); Msg: 2.7.0 Authentication successful
send: 'mail FROM:<user at domain.com> size=1711\r\n'
reply: '451 5.7.3 Must issue a STARTTLS command first\r\n'
reply: retcode (451); Msg: 5.7.3 Must issue a STARTTLS command first
send: 'rset\r\n'
192.168.100.68 - - [31/May/2007 16:14:01] "POST /roundup/issue1638
HTTP/1.1" 400 -
EXCEPTION AT Thu May 31 16:14:01 2007
Traceback (most recent call last):
  File "/usr/lib/python2.3/site-packages/roundup/scripts/roundup_server.py",
line 106, in run_cgi
    self.inner_run_cgi()
  File "/usr/lib/python2.3/site-packages/roundup/scripts/roundup_server.py",
line 266, in inner_run_cgi
    tracker.Client(tracker, self, env).main()
  File "/usr/lib/python2.3/site-packages/roundup/cgi/client.py", line
196, in main
    self.inner_main()
  File "/usr/lib/python2.3/site-packages/roundup/cgi/client.py", line
314, in inner_main
    self.mailer.exception_message()
  File "/usr/lib/python2.3/site-packages/roundup/mailer.py", line 153,
in exception_message
    self.standard_message(to, subject, content)
  File "/usr/lib/python2.3/site-packages/roundup/mailer.py", line 93,
in standard_message
    self.smtp_send(to, message)
  File "/usr/lib/python2.3/site-packages/roundup/mailer.py", line 180,
in smtp_send
    raise MessageSendError("Error: couldn't send email: %s"%msg)
MessageSendError: Error: couldn't send email: Connection unexpectedly closed