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. [EMAIL PROTECTED] 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:<[EMAIL PROTECTED]> 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:<[EMAIL PROTECTED]> 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 -- http://mail.python.org/mailman/listinfo/python-list