Issue sending email with python?

Question

I'm trying to make an email script in python. Here's what I have (from pythonlibrary.org):

#! /usr/bin/env python

import smtplib
import string

SUBJECT = "An email!"
TO = "[email protected]"
FROM = "[email protected]"
text = "This text is the contents of an email!"
BODY = string.join((
        "From: %s" % FROM,
        "To: %s" % TO,
        "Subject: %s" % SUBJECT ,
        "",
        text
        ), "\r\n")
server = smtplib.SMTP('smtp.gmail.com')
server.login('[email protected]', 'mypassword') # Not very secure, I know, but this email is dedicated to this script
server.sendmail(FROM, [TO], BODY)
server.quit()

I get smtplib.SMTPException: SMTP AUTH extension not supported by server. Is this is so, then why does smtp.gmail.com respond at all? Is this a problem with Gmail, or my script, or something else?

Error message:

Traceback (most recent call last):
  File "/Users/student/Desktop/mail.py", line 18, in <module>
    server.login('*******@gmail.com', '**************')
  File "/System/Library/Frameworks/Python.framework/Versions/2.6/lib/python2.6/smtplib.py", line 552, in login
smtplib.SMTPException: SMTP AUTH extension not supported by server.

Answer 1

You need to contact the gmail mail server on the submission port (587), not the default 25:

server = smtplib.SMTP('smtp.gmail.com', 587)

You also need to use server.starttls() before logging in (so that your password is not sent in the clear!). This is from a script I have and it works for me:

server = smtplib.SMTP()
server.connect("smtp.gmail.com", "submission")
server.starttls()
server.ehlo()
server.login(user, password)

Answer 2

Here's how to send e-mail using gmail in Python:

#!/usr/bin/env python
# -*- coding: utf-8 -*-
from email.header    import Header
from email.mime.text import MIMEText
from getpass         import getpass
from smtplib         import SMTP_SSL

login, password = '[email protected]', getpass('Gmail password:')

# create message
msg = MIMEText('message body…', _charset='utf-8')
msg['Subject'] = Header('subject…', 'utf-8')
msg['From'] = login
msg['To'] = login

# send it via gmail
s = SMTP_SSL('smtp.gmail.com', 465, timeout=10)
s.set_debuglevel(1)
try:
    s.login(login, password)
    s.sendmail(msg['From'], msg['To'], msg.as_string())
finally:
    s.quit()

Answer 3

I found I had to do an ehlo() and a starttls() before sending mail via gmail:

server = smtplib.SMTP('smtp.gmail.com', 587)
server.ehlo()
server.starttls()
server.ehlo()
server.login(SERVER_EMAIL,EMAIL_HOST_PASSWORD)

It shouldn't make a difference with the login, but I use a MIMEMultipart from email.mime.multipart for the body, with something like:

msg = MIMEMultipart('alternative')
msg['Subject'] = subject
msg['From'] = mFrom
msg['To'] = mTo
if textBody:
   part1 = MIMEText(textBody, 'plain')
   msg.attach(part1)
if htmlBody:
   part2 = MIMEText(htmlBody, 'html')
   msg.attach(part2)
BODY = msg.as_string()