Question

I use django backend to send email (but really django is irrevelant in this case), I can login via standalone client, but not via smtplib. I keep getting:

SMTPAuthenticationError (535, '5.7.0 authentication failed')

Answer 1

In my case It seems that the server lied it responded following string on hello request:

>>> conn.ehlo()
(250,
'edited.host.name Hello host.name [83.24.32.123], pleased to meet you\nENHANCEDSTATUSCODES\nPIPELINING\n8BITMIME\nSIZE\nDSN\nETRN\nAUTH GSSAPI DIGEST-MD5 CRAM-MD5 LOGIN PLAIN\nDELIVERBY\nHELP')

in which it annouced it supports CRAM-MD5 authentication method, which it didn’t.

Since I was in a hurry and resolving this issue with admin would end in missing the deadline, I had to patch SMTP class to prefer PLAIN authentication method. To do this you need to create subclass of SMTP_SSL and override login method, just copy login from SMTP class changing one line.

Change line that says:

preferred_auths = [AUTH_CRAM_MD5, AUTH_PLAIN, AUTH_LOGIN]

to:

preferred_auths = [AUTH_PLAIN, AUTH_LOGIN]

Anyway I posted the patched class: http://pastebin.com/ecL9A3P4.