Cant send email via python using gmail - smtplib.SMTPException: SMTP AUTH extension not supported by server

Question

I just want to send an email in python with an attachment

import smtplib, os
from email.MIMEMultipart import MIMEMultipart
from email.MIMEBase import MIMEBase
from email.MIMEText import MIMEText
from email.Utils import COMMASPACE, formatdate
from email import Encoders

def send_mail(send_from, send_to, subject, text, files=[], server="localhost"):
    assert type(send_to)==list
    assert type(files)==list

    msg = MIMEMultipart()
    msg['From'] = send_from
    msg['To'] = COMMASPACE.join(send_to)
    msg['Date'] = formatdate(localtime=True)
    msg['Subject'] = subject

    msg.attach( MIMEText(text) )

    for f in files:
        part = MIMEBase('application', "octet-stream")
        part.set_payload( open(f,"rb").read() )
        Encoders.encode_base64(part)
        part.add_header('Content-Disposition', 'attachment; filename="%s"' % os.path.basename(f))
        msg.attach(part)

    smtp = smtplib.SMTP('smtp.gmail.com:587')
    smtp.login('[email protected]','fu')
    smtp.sendmail(send_from, send_to, msg.as_string())
    smtp.close()

ATTACHMENTS = ['/tmp/2013-11-04-test.csv']
send_from=['[email protected]']
send_to=['[email protected]']
subject='adfadfadf'
text = 'adfadfadf'
send_mail(send_from, send_to, subject, text, files=ATTACHMENTS)

How do I auth? I have to provide a username and password. How?

Traceback (most recent call last):
  File "/home/ubuntu/workspace/miliza-devops/classes/utilities.py", line 133, in <module>
    send_mail(send_from, send_to, subject, text, files=ATTACHMENTS)
  File "/home/ubuntu/workspace/miliza-devops/classes/utilities.py", line 124, in send_mail
    smtp.login('[email protected]','fu')
  File "/usr/lib/python2.7/smtplib.py", line 576, in login
    raise SMTPException("SMTP AUTH extension not supported by server.")
smtplib.SMTPException: SMTP AUTH extension not supported by server.

Answer 1

You need a call to starttls() before you login:

smtp = smtplib.SMTP('smtp.gmail.com:587')
smtp.starttls()
smtp.login('[email protected]', 'fu')

Also, your send_from should be a str, not a list:

send_from='[email protected]'

Note that smtp.starttls() calls smtp.ehlo() implicitly:

If there has been no previous EHLO or HELO command this session, this method tries ESMTP EHLO first. https://docs.python.org/2/library/smtplib.html#smtplib.SMTP.starttls