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smtplib is broken in Python3 #49509

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smtplib is broken in Python3#49509
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bitdancer
Labels
easystdlibStandard Library Python modules in the Lib/ directorytype-bugAn unexpected behavior, bug, or error

Description

@miwa
miwa
mannequin
opened on Feb 14, 2009
BPO 5259
Nosy @loewis, @devdanzin, @bitdancer
Dependencies
  • bpo-3921: smtplib cannot sendmail over TLS
  • bpo-5304: email/base64mime.py cannot work
    		•
    Files
  • smtptest.py: smtplib test file
  • 3.0.txt: Python3.0's output of smtptest.py
  • smtplib_eol.diff: Musashi's fix as a patch
  • test-smtplib.diff: unit test
    		•

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

    Show more details

    GitHub fields:

    assignee = 'https://github.com/bitdancer'
closed_at = <Date 2009-05-28.18:51:52.597>
created_at = <Date 2009-02-14.14:19:17.380>
labels = ['easy', 'type-bug', 'library']
title = 'smtplib is broken in Python3'
updated_at = <Date 2009-05-28.18:52:20.443>
user = 'https://bugs.python.org/miwa'

    bugs.python.org fields:

    activity = <Date 2009-05-28.18:52:20.443>
actor = 'r.david.murray'
assignee = 'r.david.murray'
closed = True
closed_date = <Date 2009-05-28.18:51:52.597>
closer = 'r.david.murray'
components = ['Library (Lib)']
creation = <Date 2009-02-14.14:19:17.380>
creator = 'miwa'
dependencies = ['3921', '5304']
files = ['13088', '13092', '13783', '14043']
hgrepos = []
issue_num = 5259
keywords = ['patch', 'easy']
message_count = 12.0
messages = ['82064', '82065', '82107', '82140', '82438', '86539', '86563', '88237', '88239', '88253', '88262', '88473']
nosy_count = 8.0
nosy_names = ['loewis', 'ajaksu2', 'marcin.bachry', 'r.david.murray', 'miwa', 'kalevi', 'toastedrobot', 'j.l.caceres']
pr_nums = []
priority = 'critical'
resolution = 'fixed'
stage = 'resolved'
status = 'closed'
superseder = None
type = 'behavior'
url = 'https://bugs.python.org/issue5259'
versions = ['Python 3.0', 'Python 3.1']

    Activity

    1. miwa commented on Feb 14, 2009

      @miwa
      miwamannequin
      on Feb 14, 2009
      MannequinAuthor

      Issue #<3921> may be the same problem.

      Sending Gmail by smtplib fails on Python 3.0 and 3.0.1.
      It seems to be exist two problems in encode_plain function in smtplib.py:

      • parameter of encode_base64 must be bytes, not str,
      • by default, encode_base64 adds extra newline.
        The following is an example of patch.
      # original version
def encode_plain(user, password):
    return encode_base64("\0%s\0%s" % (user, password))

# fixed version. Note that "eol=''" is given in Python 2.6's smtplib.
def encode_plain(user, password):
    s = "\0%s\0%s" % (user, password)
    return encode_base64(s.encode('ascii'), eol='')
    2. miwa
      added
      type-crashA hard crash of the interpreter, possibly with a core dump
      stdlibStandard Library Python modules in the Lib/ directory
      on Feb 14, 2009

    3. loewis commented on Feb 14, 2009

      @loewis
      loewismannequin
      on Feb 14, 2009
      Mannequin

      Can you show us the failing application? Most likely, the bug is in your
      code, not in Python.

    4. kalevi commented on Feb 14, 2009

      @kalevi
      kalevimannequin
      on Feb 14, 2009
      Mannequin

      The attached test script works fine in Python 2.6.

      Replace the following texts in the script:
      [email protected]
      [email protected]
      password

    5. miwa commented on Feb 15, 2009

      @miwa
      miwamannequin
      on Feb 15, 2009
      MannequinAuthor

      The attachment is output of smtptest.py on Python 3.0.

    6. toastedrobot
      removed
      type-crashA hard crash of the interpreter, possibly with a core dump
      on Feb 18, 2009
    7. toastedrobot
      changed the title [-]smtplib is broken in Python3[/-] [+]gmail smtp[/+] on Feb 18, 2009

    8. toastedrobot commented on Feb 18, 2009

      @toastedrobot
      toastedrobotmannequin
      on Feb 18, 2009
      Mannequin

      sorry, pressed the wrong button.

      that solution does work. didn't find this until #python helped me get:

      return encode_base64( ("\0%s\0%s" % (user, password) ).encode('ascii') )

    9. toastedrobot
      added
      type-crashA hard crash of the interpreter, possibly with a core dump
      on Feb 18, 2009
    10. toastedrobot
      changed the title [-]gmail smtp[/-] [+]smtplib is broken in Python3[/+] on Feb 18, 2009
    11. devdanzin
      added
      easy
      type-bugAn unexpected behavior, bug, or error
      and removed
      type-crashA hard crash of the interpreter, possibly with a core dump
      on Apr 22, 2009

    12. marcinbachry commented on Apr 25, 2009

      @marcinbachry
      marcinbachrymannequin
      on Apr 25, 2009
      Mannequin

      I add simple smtp auth unit test to exercise this bug.

    13. devdanzin commented on Apr 25, 2009

      @devdanzin
      devdanzinmannequin
      on Apr 25, 2009
      Mannequin

      Martin: see a test script in bpo-3921.

    14. bitdancer commented on May 23, 2009

      @bitdancer
      bitdancer
      on May 23, 2009
      Member

      5304 and 3921 are fixed. Is there still an issue here? If so, I think
      we need a test case we can add to the test suite. It can be a patch
      against the new test_smtpnet.py test.

    15. bitdancer commented on May 23, 2009

      @bitdancer
      bitdancer
      on May 23, 2009
      Member

      Looks like I accidentally deleted the file I was asking for. Not sure
      how that happened, but I'm reattaching it.

    16. bitdancer
      self-assigned this
      on May 23, 2009

    17. jlcaceres commented on May 23, 2009

      @jlcaceres
      jlcaceresmannequin
      on May 23, 2009
      Mannequin

      There is a similar problem that I found with encode_cram_md5 in
      smtplib.py, SMTP.login() method. I used the solution proposed by miwa,
      both for PLAIN and CRAM MD5 authentication. Additionally, for the last
      one, I had to introduce a second correction and byte encode the
      password string when passing it to hmac.HMAC.

      I do not know if I did things correctly, but just in case it can help
      here is the complete patch that I used and worked well with the two
      AUTH methods. I keep the original and modified lines for clarity.

      def encode_cram_md5(challenge, user, password):
            challenge = base64.decodestring(challenge)
            #response = user + " " + hmac.HMAC(password,    
challenge).hexdigest()
            response = user + " " + hmac.HMAC(password.encode(), 
challenge).hexdigest()
            #return encode_base64(response)
            return encode_base64((response).encode('ascii'), eol='')
            
        def encode_plain(user, password):
            #return encode_base64("\0%s\0%s" % (user, password))
            return encode_base64(("\0%s\0%s" % (user, password)).encode
('ascii'), eol='')

    18. bitdancer commented on May 24, 2009

      @bitdancer
      bitdancer
      on May 24, 2009
      Member

      Committed the simple auth tests and fix in r72868 in py3k and r72877 in
      3.0. Also added the test to trunk in r72878 to keep the test source in
      sync, and to 26maint similarly in r72886.

      Now we need tests for the other auth cases.

    19. bitdancer commented on May 28, 2009

      @bitdancer
      bitdancer
      on May 28, 2009
      Member

      LOGIN and CRAM-MD5 login are fixed in r72990 (3.1) and r72991 (3.0).

    20. bitdancer
      closed this as completedon May 28, 2009
    21. ezio-melotti
      transferred this issue fromon Apr 10, 2022
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