How to Send Smtp Email for Office365 With Python Using Tls/Ssl

send SMTP email for office365 with python using tls/ssl

Vishesh Arya!

SMTP AUTH extension not supported by Office 365 account. Search for Microsoft Graph to do this.

SMTP email for office365

You need a \n between subject and email body in the 3rd argument to sendmail

msg = 'Subject: Email Subject.\n{}'.format('this is a message')
mailserver.sendmail('myemail@company.com','receiver@company.com', msg)

Errors when using SMTPLIB SSL email with a 365 email address

From the documentation of SMTP_SSL:

SMTP_SSL should be used for situations where SSL is required from the beginning of the connection and using starttls() is not appropriate.

Thus, SMTP_SSL is for implicit SMTP and the common port for this is 465. Port 587 is instead used for explicit SMTP where a plain connect is done and later an upgrade to SSL with the STARTTLS command.

What happens here is that the client tries to speak SSL/TLS to a server which does not expect SSL/TLS at this stage and thus replies with non-TLS data. These get interpreted as TlS nonetheless which results in this strange [SSL: WRONG_VERSION_NUMBER].

To fix this either use port 465 (and not 587) with SMTP_SSL (not supported by Office365) or use port 587 but with starttls:

with smtplib.SMTP("smtp.office365.com", 587) as server:
     server.starttls(context=context)

SSL error while sending email using smtp with Python

Microsoft Outlook uses STARTTLS when sending an email. So you need to replace smtplib.SMTP_SSL with smtplib.SMTP and you need to call starttls

reference: smtplib.SMTP.starttls

import smtplib
from email.message import EmailMessage

sender = 'somename@outlook.com'
recipient = 'somename@gmail.com'

msg = EmailMessage()
msg.set_content('this is a test')
msg['From'] = 'somename@outlook.com'
msg['To'] = 'somename@gmail.com'
msg['Subject'] = 'test email'

with smtplib.SMTP('smtp.office365.com', 587) as server:
    server.ehlo()
    server.starttls()
    server.ehlo()
    server.ehlo()
    server.login('your_login', "your_password", initial_response_ok=True) 
    server.ehlo()
    server.sendmail(sender, recipient, msg.as_string())
    print('Email sent!')
    server.close()

Here is the Outlook message in my Gmail account.

I noted that I had to change my Outlook password, because it had a \n, which Python read as a new line.

----------------------------------------
My system information
----------------------------------------
Platform:       macOS
OS Version:     10.15.7
Python Version: 3.9
----------------------------------------

Your question didn't identity the type of Outlook account you have.

1. Free account
2. Corporate account

You stated in the comments below that your error message included ask your email administrator. I haven't seem this message with the Free account so I'm assuming that you might have a Corporate account. If you do have the latter please review this Enable or disable authenticated client SMTP submission, because an email administrator would need to enable Authenticated SMTP on your corporate account.

python: smtp with TLS delivers no message

Your message is not a valid mail message, which consists of a header and a body. Try something like this:

msg = """From: <me@example.com>
To: <you@example.com>
Subject: foo

This is a test email 
"""

Django: send email via Office365

To send email using the Office365 smtp server, the "from" user and the "host" user must be the same. So I added this setting in Django in order to send email to the admins:

SERVER_EMAIL = EMAIL_HOST_USER

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