smtplib cannot sendmail over TLS

@devdanzin

BPO	3921
Nosy	@devdanzin
Superseder	bpo-5259: smtplib is broken in Python3
Files	sendmail_test.py smtplib.diff: Quick and dirty workaround smtpbug.py: Example script

^{Note: these values reflect the state of the issue at the time it was migrated and might not reflect the current state.}

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GitHub fields:

assignee = None
closed_at = <Date 2009-04-25.22:44:26.762>
created_at = <Date 2008-09-21.08:11:47.474>
labels = ['easy', 'type-bug', 'library']
title = 'smtplib cannot sendmail over TLS'
updated_at = <Date 2009-04-25.22:44:26.761>
user = 'https://bugs.python.org/shidot'

bugs.python.org fields:

activity = <Date 2009-04-25.22:44:26.761>
actor = 'ajaksu2'
assignee = 'none'
closed = True
closed_date = <Date 2009-04-25.22:44:26.762>
closer = 'ajaksu2'
components = ['Library (Lib)']
creation = <Date 2008-09-21.08:11:47.474>
creator = 'shidot'
dependencies = []
files = ['11540', '13736', '13782']
hgrepos = []
issue_num = 3921
keywords = ['patch', 'easy']
message_count = 5.0
messages = ['73504', '82339', '86296', '86560', '86561']
nosy_count = 3.0
nosy_names = ['ajaksu2', 'shidot', 'miwa']
pr_nums = []
priority = 'high'
resolution = 'duplicate'
stage = 'test needed'
status = 'closed'
superseder = '5259'
type = 'behavior'
url = 'https://bugs.python.org/issue3921'
versions = ['Python 3.0', 'Python 3.1']

when a SMTP object tries to send a mail through TLS, the smtp server
replies retcode 502.

When a test code (sendmail_test.py) is executed on Python 3,
it stacks on sending mail while the test code works on Python 2.5.

Following is the result of the test.

The first half is the result on Python 2.5.
A mail has been sent without any problem.

The second half is the result on Python 3.
Upto AUTH, it works fine.
But when it sends mail, the server replies retcode 502.
This is the message of failure:

send: 'mail FROM:<[email protected]> size=176\r\n'
reply: b'502 5.5.1 Unrecognized command. u8sm8612791tia.6\r\n'

====================== RESULT ============================
Z:\doc\monthly\08-09\py_book3\script\net>python mail2.py
send: 'ehlo [192.168.1.8]\r\n'
reply: '250-mx.google.com at your service, [124.41.68.137]\r\n'
reply: '250-SIZE 35651584\r\n'
reply: '250-8BITMIME\r\n'
reply: '250-STARTTLS\r\n'
reply: '250 ENHANCEDSTATUSCODES\r\n'
reply: retcode (250); Msg: mx.google.com at your service, [124.41.68.137]
SIZE 35651584
8BITMIME
STARTTLS
ENHANCEDSTATUSCODES
send: 'STARTTLS\r\n'
reply: '220 2.0.0 Ready to start TLS\r\n'
reply: retcode (220); Msg: 2.0.0 Ready to start TLS
send: 'ehlo [192.168.1.8]\r\n'
reply: '250-mx.google.com at your service, [124.41.68.137]\r\n'
reply: '250-SIZE 35651584\r\n'
reply: '250-8BITMIME\r\n'
reply: '250-AUTH LOGIN PLAIN\r\n'
reply: '250 ENHANCEDSTATUSCODES\r\n'
reply: retcode (250); Msg: mx.google.com at your service, [124.41.68.137]
SIZE 35651584
8BITMIME
AUTH LOGIN PLAIN
ENHANCEDSTATUSCODES
send: 'AUTH PLAIN AGxhbWJkYS5sZXRAZ21haWwuY29tAGNoaWtha29zMDA=\r\n'
reply: '235 2.7.0 Accepted\r\n'
reply: retcode (235); Msg: 2.7.0 Accepted
send: 'mail FROM:<[email protected]> size=176\r\n'
reply: '250 2.1.0 OK\r\n'
reply: retcode (250); Msg: 2.1.0 OK
send: 'rcpt TO:<[email protected]>\r\n'
reply: '250 2.1.5 OK\r\n'
reply: retcode (250); Msg: 2.1.5 OK
send: 'data\r\n'
reply: '354 Go ahead\r\n'
reply: retcode (354); Msg: Go ahead
data: (354, 'Go ahead')
send: 'MIME-Version: 1.0\r\nContent-Type: text/plain;
charset="us-ascii"\r\nCon
ent-Transfer-Encoding: 7bit\r\nFrom: [email protected]\r\nTo:
takafumi@shido
info\r\nSubject: test\r\n\r\nThis is a test.\r\n.\r\n'
reply: '250 2.0.0 OK 1221982163 22sm8756554tim.10\r\n'
reply: retcode (250); Msg: 2.0.0 OK 1221982163 22sm8756554tim.10
data: (250, '2.0.0 OK 1221982163 22sm8756554tim.10')
send: 'quit\r\n'
reply: '221 2.0.0 mx.google.com closing connection 22sm8756554tim.10\r\n'
reply: retcode (221); Msg: 2.0.0 mx.google.com closing connection
22sm8756554ti
.10

Z:\doc\monthly\08-09\py_book3\script\net>py3 mail2.py

Z:\doc\monthly\08-09\py_book3\script\net>c:\python30\python.exe mail2.py

send: 'ehlo [192.168.1.8]\r\n'
reply: b'250-mx.google.com at your service, [124.41.68.137]\r\n'
reply: b'250-SIZE 35651584\r\n'
reply: b'250-8BITMIME\r\n'
reply: b'250-STARTTLS\r\n'
reply: b'250 ENHANCEDSTATUSCODES\r\n'
reply: retcode (250); Msg: b'mx.google.com at your service,
[124.41.68.137]\nSI
E 35651584\n8BITMIME\nSTARTTLS\nENHANCEDSTATUSCODES'
send: 'STARTTLS\r\n'
reply: b'220 2.0.0 Ready to start TLS\r\n'
reply: retcode (220); Msg: b'2.0.0 Ready to start TLS'
send: 'ehlo [192.168.1.8]\r\n'
reply: b'250-mx.google.com at your service, [124.41.68.137]\r\n'
reply: b'250-SIZE 35651584\r\n'
reply: b'250-8BITMIME\r\n'
reply: b'250-AUTH LOGIN PLAIN\r\n'
reply: b'250 ENHANCEDSTATUSCODES\r\n'
reply: retcode (250); Msg: b'mx.google.com at your service,
[124.41.68.137]\nSI
E 35651584\n8BITMIME\nAUTH LOGIN PLAIN\nENHANCEDSTATUSCODES'
send: 'AUTH PLAIN AGxhbWJkYS5sZXRAZ21haWwuY29tAGNoaWtha29zMDA=\n\r\n'
reply: b'235 2.7.0 Accepted\r\n'
reply: retcode (235); Msg: b'2.7.0 Accepted'
send: 'mail FROM:<[email protected]> size=176\r\n'
reply: b'502 5.5.1 Unrecognized command. u8sm8612791tia.6\r\n'
reply: retcode (502); Msg: b'5.5.1 Unrecognized command. u8sm8612791tia.6'
send: 'rset\r\n'
reply: b'250 2.1.0 OK\r\n'
reply: retcode (250); Msg: b'2.1.0 OK'
Traceback (most recent call last):
  File "sendmail_test.py", line 43, in <module>

File "sendmail_test.py", line 35, in send_mail

File "c:\python30\lib\smtplib.py", line 701, in sendmail
raise SMTPSenderRefused(code, resp, from_addr)
smtplib.SMTPSenderRefused: (502, b'5.5.1 Unrecognized command.
u8sm8612791tia.6
, '[email protected]')

Z:\doc\monthly\08-09\py_book3\script\net>

==================== Test Code (sendmail_test.py) =============

#! python

''' send mail using Python 2.5 and 3'''

import smtplib
from email.mime.text import MIMEText
from email.header import Header


def make_mime_text(mail_from, mail_to, subject, body):
    '''create MIMEText'''

    msg = MIMEText(body, 'plain', 'ascii')
    msg['From'] = Header(mail_from, 'ascii')
    msg['To'] = Header(mail_to,  'ascii')
    msg['Subject'] = Header(subject, 'ascii')
    return msg

def send_mail(server, mail_from, mail_to, msg, use_tls=False, user='',
passwd='', ):
    '''sendmail, if use_tls=True, use TLS'''

    sender = smtplib.SMTP(server, (587 if use_tls else 25))
    sender.set_debuglevel(1)
    
    if use_tls:
        sender.ehlo()
        sender.starttls()
        sender.ehlo()
        sender.login(user, passwd)
        
    sender.sendmail(mail_from, mail_to, msg.as_string())
    sender.quit()


if __name__ =='__main__':
    ME = '[email protected]'
    TK = '[email protected]'
    send_mail('smtp.gmail.com', ME, (TK,), \
      make_mime_text(ME, TK, "test", "This is a test."), True, ME,
'********')

The difference is this line.

(2.5, work)
send: 'AUTH PLAIN AGxhbWJkYS5sZXRAZ21haWwuY29tAGNoaWtha29zMDA=\r\n'

(Python3, error)
send: 'AUTH PLAIN AGxhbWJkYS5sZXRAZ21haWwuY29tAGNoaWtha29zMDA=\n\r\n'

The attached patch makes using smtplib in py3k possible. It isn't
proposed as a correct fix.

As pointed by Mariano on IRC, this is closely related to bpo-5259 and bpo-5304.

Actually, this is fixed by the patch in bpo-5259 (also has test).

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smtplib cannot sendmail over TLS #48171

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smtplib cannot sendmail over TLS #48171

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shidot commented on Sep 21, 2008

miwa commented on Feb 17, 2009

devdanzin commented on Apr 22, 2009

devdanzin commented on Apr 25, 2009

devdanzin commented on Apr 25, 2009

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