smtplib on linux fails to log in correctly

[1kastner]

BPO	31302
Nosy	@1kastner

^{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 = None
created_at = <Date 2017-08-29.12:56:45.003>
labels = ['type-bug', 'library']
title = 'smtplib on linux fails to log in correctly'
updated_at = <Date 2017-08-29.13:18:18.791>
user = 'https://github.com/1kastner'

bugs.python.org fields:

activity = <Date 2017-08-29.13:18:18.791>
actor = 'murphdasurf'
assignee = 'none'
closed = False
closed_date = None
closer = None
components = ['Library (Lib)']
creation = <Date 2017-08-29.12:56:45.003>
creator = 'murphdasurf'
dependencies = []
files = []
hgrepos = []
issue_num = 31302
keywords = []
message_count = 2.0
messages = ['300986', '300987']
nosy_count = 1.0
nosy_names = ['murphdasurf']
pr_nums = []
priority = 'normal'
resolution = None
stage = None
status = 'open'
superseder = None
type = 'behavior'
url = 'https://bugs.python.org/issue31302'
versions = ['Python 3.6']

[1kastner]

The protocol should run like this:

send: 'ehlo XXXXXXXXXXXXX\r\n'
reply: b'250-XXXXXXXXXXXXXXXXXX.com\r\n'
reply: b'250-PIPELINING\r\n'
reply: b'250-SIZE 100480000\r\n'
reply: b'250-VRFY\r\n'
reply: b'250-ETRN\r\n'
reply: b'250-STARTTLS\r\n'
reply: b'250-ENHANCEDSTATUSCODES\r\n'
reply: b'250-8BITMIME\r\n'
reply: b'250 DSN\r\n'
reply: retcode (250); Msg: b'XXXXXXXXXXXXXXXX.com\nPIPELINING\nSIZE 100480000\nVRFY\nETRN\nSTARTTLS\nENHANCEDSTATUSCODES\n8BITMIME\nDSN'
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 XXXXXXXXXXXXXXXXXXXXX\r\n'
reply: b'250-XXXXXXXXXXXXXXXXXX.com\r\n'
reply: b'250-PIPELINING\r\n'
reply: b'250-SIZE 100480000\r\n'
reply: b'250-VRFY\r\n'
reply: b'250-ETRN\r\n'
reply: b'250-AUTH LOGIN\r\n'
reply: b'250-AUTH=LOGIN\r\n'
reply: b'250-ENHANCEDSTATUSCODES\r\n'
reply: b'250-8BITMIME\r\n'
reply: b'250 DSN\r\n'
reply: retcode (250); Msg: b'XXXXXXXXXXXXXXXXXXXXXX.com\nPIPELINING\nSIZE 100480000\nVRFY\nETRN\nAUTH LOGIN\nAUTH=LOGIN\nENHANCEDSTATUSCODES\n8BITMIME\nDSN'
send: 'AUTH LOGIN XXXXXXXXXXXXXXX\r\n'
reply: b'334 RRRRRRRRRRR\r\n'
reply: retcode (334); Msg: b'RRRRRRRRR'
send: 'TTTTTTTTTTTT=\r\n'
reply: b'235 2.7.0 Authentication successful\r\n'
reply: retcode (235); Msg: b'2.7.0 Authentication successful'

And in fact it does so on Windows. However, on Linux it runs like this:

send: 'ehlo XXXXXXXXXXXXX\r\n'
reply: b'250-XXXXXXXXXXXXX.com\r\n'
reply: b'250-PIPELINING\r\n'
reply: b'250-SIZE 100480000\r\n'
reply: b'250-VRFY\r\n'
reply: b'250-ETRN\r\n'
reply: b'250-STARTTLS\r\n'
reply: b'250-ENHANCEDSTATUSCODES\r\n'
reply: b'250-8BITMIME\r\n'
reply: b'250 DSN\r\n'
reply: retcode (250); Msg: b'XXXXXXXXXXXXX.com\nPIPELINING\nSIZE 100480000\nVRFY\nETRN\nSTARTTLS\nENHANCEDSTATUSCODES\n8BITMIME\nDSN'
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 XXXXXXXXXXXXX\r\n'
reply: b'250-XXXXXXXXXXXXX.com\r\n'
reply: b'250-PIPELINING\r\n'
reply: b'250-SIZE 100480000\r\n'
reply: b'250-VRFY\r\n'
reply: b'250-ETRN\r\n'
reply: b'250-AUTH LOGIN\r\n'
reply: b'250-AUTH=LOGIN\r\n'
reply: b'250-ENHANCEDSTATUSCODES\r\n'
reply: b'250-8BITMIME\r\n'
reply: b'250 DSN\r\n'
reply: retcode (250); Msg: b'XXXXXXXXXXXXX.com\nPIPELINING\nSIZE 100480000\nVRFY\nETRN\nAUTH LOGIN\nAUTH=LOGIN\nENHANCEDSTATUSCODES\n8BITMIME\nDSN'
send: 'AUTH LOGIN XXXXXXXXXXXXXXX\r\n'
reply: b'334 RRRRRRRRRRR\r\n'
reply: retcode (334); Msg: b'RRRRRRRRRRR'
send: "b''\r\n"
reply: b'535 5.7.8 Error: authentication failed: another step is needed in authentication\r\n'
reply: retcode (535); Msg: b'5.7.8 Error: authentication failed: another step is needed in authentication'

The last sent message is an empty string and then the authentication fails. All other tokens which are replaced by XXXXXX, RRRRR or TTTTT are exactly the same.

This way the login fails and I can not use smtplib to send my mail.

[1kastner]

PS: The corresponding code is:

server_ssl = smtplib.SMTP(SERVER, PORT)
server_ssl.set_debuglevel(True)
server_ssl.ehlo()
server_ssl.starttls()
server_ssl.login(USER_FOR_AUTHENTICATION, XXXXXX)