Monday, October 23, 2017

Gmail blocks login attempt from Python with app specific password

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I'm trying to send an email from a Google account using Python's smtplib, but getting an error, and now I'm kind of at a loss. Google responds with the following: Please log in via your web browser and then try again. Learn more at https://support.google.com/mail/answer/78754.

The account has two factor authentication enabled, so I'm using an app specific password for my login. To my understanding, this should then work without enabling the setting for less secure apps, shouldn't it? I've been doing the same with another account while testing without a problem, but now I finally got the credentials for the proper account and there it won't accept the authentication.

I'm aware that there is a Python Gmail API thingy to use with OAuth, but if at all possible I don't want to include more packages and rewrite much, and I don't really want to enable the "less secure apps" setting either. Is there a way to get this working without either?

If it makes a difference, here is the code I use for sending email. As said before, this was working fine with another account, so I'm not sure if it's actually relevant.

def send_mail(to_address, subject, body):     smtp_user = "myaccount@domain.com"     smtp_password = "MyAppPasswordFromGoogle"     server = "smtp.gmail.com"     port = 587      msg = MIMEMultipart("alternative")     msg["Subject"] = subject     msg["From"] = smtp_user     msg["To"] = to_address     msg.attach(MIMEText(body, "html"))     s = smtplib.SMTP(server, port)     s.connect(server, port)     s.ehlo()     s.starttls()     s.ehlo()     s.login(smtp_user, smtp_password)     s.sendmail(smtp_user, to_address, msg.as_string())     s.quit() 

Edit: There is an interesting difference between the two accounts: on https://myaccount.google.com/lesssecureapps, my old (working) one says "this setting isn't available for accounts that have two factor authentication enabled", while the new one says "this setting is managed by your domain administrator", even though both use 2FA and it's also forced in both domains. So I suppose there is some setting that the domain admin has to change, but I don't know which one that would be.

3 Answers

Answers 1

I tried replicating exactly your case (with an account that has a two factor authentication enabled). After creating my app password, I used it in the code.

Anyway, I think your problem is this:

s = smtplib.SMTP(server, port) s.connect(server, port) 

You execute 2 times the connection.

Try with

s = smtplib.SMTP() s.connect(server, port) 

or just this

s = smtplib.SMTP(server, port) 

The entire code:

import smtplib from email.mime.multipart import MIMEMultipart from email.mime.text import MIMEText   smtp_user = 'myUser@gmail.com' smtp_password = 'my16charactersAppPassword' server = 'smtp.gmail.com' port = 587 msg = MIMEMultipart("alternative") msg["Subject"] = 'Why,Oh why!' msg["From"] = smtp_user msg["To"] = "destinationUser@gmail.com" msg.attach(MIMEText('\nsent via python', 'plain')) s = smtplib.SMTP(server, port) s.ehlo() s.starttls() s.login(smtp_user, smtp_password) s.sendmail(smtp_user, "destinationUser@gmail.com", msg.as_string()) s.quit() 

Answers 2

I am just curious if you have enabled IMAP (despite of the fact that SMTP has nothing to do with IMAP)...

Here is an old list with many different solutions - Sending email through Gmail SMTP server with C#

Answers 3

Seems simple, but check to make sure Allow less secure apps is enabled.

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