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@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.loca l\r\n'
reply: '250-smtpx15.msoutlo okonline.net Hello [202.173.131.223]\r\n'
reply: '250-SIZE 31457280\r\n'
reply: '250-PIPELINING\r\n'
reply: '250-ENHANCEDSTATUSC ODES\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.msoutlo okonline.net Hello [202.173.131.223]
SIZE 31457280
PIPELINING
ENHANCEDSTATUSC ODES
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@doma in.comsize=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.loca l\r\n'
reply: '250-smtpx15.msoutlo okonline.net Hello [202.173.131.223]\r\n'
reply: '250-SIZE 31457280\r\n'
reply: '250-PIPELINING\r\n'
reply: '250-ENHANCEDSTATUSC ODES\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.msoutlo okonline.net Hello [202.173.131.223]
SIZE 31457280
PIPELINING
ENHANCEDSTATUSC ODES
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@doma in.comsize=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.exc eption_message( )
File "/usr/lib/python2.3/site-packages/roundup/mailer.py", line 153,
in exception_messa ge
self.standard_m essage(to, subject, content)
File "/usr/lib/python2.3/site-packages/roundup/mailer.py", line 93,
in standard_messag e
self.smtp_send( to, message)
File "/usr/lib/python2.3/site-packages/roundup/mailer.py", line 180,
in smtp_send
raise MessageSendErro r("Error: couldn't send email: %s"%msg)
MessageSendErro r: Error: couldn't send email: Connection unexpectedly closed

[Tijs]

Re: Roundup, smtplib, TLS and MS Exchange

carlistixx wrote:

[foobar@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

I think this must be an issue with roundup, issuing commands in the wrong
order. The correct order should (according to the rfc and the python docs)
be:
* ehlo()
* starttls()
* ehlo()
* login()
....

--

Regards,
Tijs

[carlistixx]

Re: Roundup, smtplib, TLS and MS Exchange

Thanks for your response. I tried modifying the Roundup code as suggested:

class SMTPConnection( smtplib.SMTP):
''' Open an SMTP connection to the mailhost specified in the config
'''
def __init__(self, config):

smtplib.SMTP.__ init__(self, config.MAILHOST )
self.set_debugl evel(1)
# start the TLS if requested
if config["MAIL_TLS"]:
self.ehlo()
self.starttls(c onfig["MAIL_TLS_KEYFI LE"],
config["MAIL_TLS_CERTF ILE"])
self.ehlo()

# ok, now do we also need to log in?
mailuser = config["MAIL_USERN AME"]
if mailuser:
self.login(mail user, config["MAIL_PASSW ORD"])

I've inserted a call to ehlo() before and after the call to
starttls(). Adding the first call to ehlo() does help - I don't get so
many complaints from the server. But it still doesn't work- it seems
like the server stops responding after the call to starttls().

I have not specified a keyfile or certfile in the Roundup
configuration, but as I understand it these are optional, so I presume
this is not causing the problem.

[foobar@moe tracker]$ roundup-server -p 8081
roundup=/home/foobar/roundup/tracker
Roundup server started on :8081
send: 'ehlo moe.foobar.loca l\r\n'
reply: '250-smtpx15.msoutlo okonline.net Hello [202.173.131.223]\r\n'
reply: '250-SIZE 31457280\r\n'
reply: '250-PIPELINING\r\n'
reply: '250-ENHANCEDSTATUSC ODES\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.msoutlo okonline.net Hello [202.173.131.223]
SIZE 31457280
PIPELINING
ENHANCEDSTATUSC ODES
STARTTLS
AUTH LOGIN
8BITMIME
BINARYMIME
CHUNKING
send: 'STARTTLS\r\n'
reply: '220 2.0.0 SMTP server ready\r\n'
reply: retcode (220); Msg: 2.0.0 SMTP server ready
send: 'ehlo moe.foobar.loca l\r\n'
send: 'ehlo moe.foobar.loca l\r\n'
reply: '250-smtpx15.msoutlo okonline.net Hello [202.173.131.223]\r\n'
reply: '250-SIZE 31457280\r\n'
reply: '250-PIPELINING\r\n'
reply: '250-ENHANCEDSTATUSC ODES\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.msoutlo okonline.net Hello [202.173.131.223]
SIZE 31457280
PIPELINING
ENHANCEDSTATUSC ODES
STARTTLS
AUTH LOGIN
8BITMIME
BINARYMIME
CHUNKING
send: 'STARTTLS\r\n'
reply: '220 2.0.0 SMTP server ready\r\n'
reply: retcode (220); Msg: 2.0.0 SMTP server ready
send: 'ehlo moe.foobar.loca l\r\n'
192.168.100.68 - - [04/Jun/2007 10:43:24] "POST /roundup/issue1638
HTTP/1.1" 400 -
EXCEPTION AT Mon Jun 4 10:43:24 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.exc eption_message( )
File "/usr/lib/python2.3/site-packages/roundup/mailer.py", line 153,
in exception_messa ge
self.standard_m essage(to, subject, content)
File "/usr/lib/python2.3/site-packages/roundup/mailer.py", line 93,
in standard_messag e
self.smtp_send( to, message)
File "/usr/lib/python2.3/site-packages/roundup/mailer.py", line 173,
in smtp_send
smtp = SMTPConnection( self.config)
File "/usr/lib/python2.3/site-packages/roundup/mailer.py", line 194,
in __init__
self.ehlo()
File "/usr/lib/python2.3/smtplib.py", line 390, in ehlo
(code,msg)=self .getreply()
File "/usr/lib/python2.3/smtplib.py", line 344, in getreply
line = self.file.readl ine()
File "/usr/lib/python2.3/smtplib.py", line 159, in readline
chr = self.sslobj.rea d(1)
sslerror: The read operation timed out





On 6/1/07, Tijs <tijs_news@blue scraper.nlwrote :

carlistixx wrote:
>

[foobar@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

>
I think this must be an issue with roundup, issuing commands in the wrong
order. The correct order should (according to the rfc and the python docs)
be:
* ehlo()
* starttls()
* ehlo()
* login()
...
>
--
>
Regards,
Tijs
--

http://mail.python.org/mailman/listinfo/python-list

>