Cannot send email via python using gmail - smtplib.SMTPException: SMTP extension AUTH is not supported by the 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('[e-mail]','fu')
    smtp.sendmail(send_from, send_to, msg.as_string())
    smtp.close()

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

How do I log in? I must 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('[e-mail]','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 to call starttls()before entering the system:

smtp = smtplib.SMTP('smtp.gmail.com:587')
smtp.starttls()
smtp.login('[e-mail]', 'fu')

In addition, yours send_fromshould be str, not list:

send_from='[e-mail]'

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

EHLO HELO, ESMTP EHLO. https://docs.python.org/2/library/smtplib.html#smtplib.SMTP.starttls

Answer 2

gmail smtp.ehlo() smtp.starttls() Gmail Python?