Question

I am trying to send email (Gmail) using python, but I am getting following error.

Traceback (most recent call last):  
File "emailSend.py", line 14, in <module>  
server.login(username,password)  
File "/usr/lib/python2.5/smtplib.py", line 554, in login  
raise SMTPException("SMTP AUTH extension not supported by server.")  
smtplib.SMTPException: SMTP AUTH extension not supported by server.

The Python script is the following.

import smtplib

fromaddr = '[e-mail]'
toaddrs  = '[e-mail]'
msg = 'Why,Oh why!'
username = '[e-mail]'
password = 'pwd'
server = smtplib.SMTP('smtp.gmail.com:587')
server.starttls()
server.login(username,password)
server.sendmail(fromaddr, toaddrs, msg)
server.quit()

Answer 1

You need to say EHLO before just running straight into STARTTLS:

server = smtplib.SMTP('smtp.gmail.com:587')
server.ehlo()
server.starttls()

---

Also you should really create From:, To: and Subject: message headers, separated from the message body by a blank line and use CRLF as EOL markers.

E.g.

msg = "\r\n".join([
  "From: [e-mail]",
  "To: [e-mail]",
  "Subject: Just a message",
  "",
  "Why, oh why"
  ])

Note:

In order for this to work you need to enable "Allow less secure apps" option in your gmail account configuration. Otherwise you will get a "critical security alert" when gmail detects that a non-Google apps is trying to login your account.