How to send an email with Gmail as provider using Python?

Question

I'm attempting to send an email (Gmail) through python, however, I am getting the 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.

Look at the below python script:

import smtplib

fromaddr = '[email protected]'

toaddrs  = '[email protected]'

msg = 'Why,Oh why!'

username = '[email protected]'

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 want to just say EHLO before running straight into STARTTLS: 

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

server.ehlo()

server.starttls()

Additionally, you should make From:, To: and Subject: message headers, isolated from the message body by a clear line and use CRLF as EOL markers. 

Example:

msg = "\r\n".join([

  "From: [email protected]",

  "To: [email protected]",

  "Subject: Just a message",

  "",

  "Why, oh why"

  ])

Note:

With the goal for this to work you want to enable the "allow less secure applications" choice in your Gmail account configuration. Else you will get a "basic security alert" when Gmail identifies that a non-Google application is attempting to login to your account.

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