Send a email through googleapi gmail python using oauth2

Question

I'm trying to send a email as a user using OAuth 2. On Google's website they state:

This document defines the SASL XOAUTH2 mechanism for use with the IMAP AUTHENTICATE and SMTP AUTH commands. This mechanism allows the use of OAuth 2.0 Access Tokens to authenticate to a user's Gmail account.

Using the tests provided in their oauth2.py

smtp_conn = smtplib.SMTP('smtp.gmail.com', 587)
smtp_conn.set_debuglevel(True)
smtp_conn.ehlo('test')
smtp_conn.starttls()
smtp_conn.docmd('AUTH', 'XOAUTH2 ' + base64.b64encode(auth_string))

where you can test whether or not you can connect to their smtp servers using a provided access token it succeeds, but when I try to send a email using sendmail I get a failure.

If I add smtp_conn.sendmail('[email protected]', '[email protected]', 'msg') it says that I need to authenticate.

From the docs am I not authenticating when I send the AUTH command with the required auth string?

Thanks.

UPDATE *

So apparently if I re authenticate in the catch of a try catch statement it works.. Any ideas?

try:
    smtp_conn.sendmail('[email protected]', '[email protected]', 'cool')
except:
    smtp_conn.docmd('AUTH', 'XOAUTH2 ' + base64.b64encode(auth_string))
    smtp_conn.sendmail('[email protected]', '[email protected]', 'cool')

You should be using [email protected]. [email protected] may be a real email address, in which case you may be spamming them. — Nathan Villaescusa
– Nathan Villaescusa, Commented Oct 11, 2012 at 19:42
those are just sample emails to show how the code works.... when I actually run the code I use my own emails — mirugai
– mirugai, Commented Oct 11, 2012 at 20:13

Andres Restrepo · Accepted Answer · 2012-10-17 04:29:03Z

1

You need another ehlo call after starttls. So:

    smtp_conn = smtplib.SMTP('smtp.gmail.com', 587)
    smtp_conn.set_debuglevel(True)
    smtp_conn.ehlo()
    smtp_conn.starttls()
    smtp_conn.ehlo()
    smtp_conn.docmd('AUTH', 'XOAUTH2 ' + base64.b64encode(auth_string))

answered Oct 17, 2012 at 4:29

Andres Restrepo

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1 Comment

mirugai Over a year ago

how come you have to do that twice? and if so how does that try catch work?

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