smtplib.SMTPNotSupportedError: SMTP AUTH extension not supported by server - python-3.7

Question

I am a python newbie trying to email using Python 3.7.
I am referring to the following python web page to put together my code.
https://docs.python.org/3.7/library/email.examples.html
I am not able to understand what is wrong. Do I have to update any settings in Outlook for the email to go through? Weird that the above documentation doesn't mention anything about my email password
#!/usr/bin/env python3
import smtplib
from email.message import EmailMessage
body = "Hello User,\nThis is to notify you that...."
msg = EmailMessage()
msg.set_content(body)
msg['Subject'] = 'Name Clash.....'
msg['From'] = 'pukav#outlook.com'
msg['To'] = 'iampukav#gmail.com'
s = smtplib.SMTP('smtp-mail.outlook.com', 587)
s.login('pukav#outlook.com', 'mypassword')
s.send_message(msg)
s.quit()
ERRORS:
in login "SMTP AUTH extension not supported by server."
smtplib.SMTPNotSupportedError: SMTP AUTH extension not supported by server.

Answer 1

I had the same error for Gmail server and found the solution below.
(I am not sure this solution will be perfectly shaped for Outlook)
import smtplib
from typing import List
SMTP_HOST = "smtp.gmail.com"
SMTP_PORT = 587
def send_email(from_addr: str, to_addr: List[str], subject: str) -> None:
msg = f"From: {from_addr}\r\nTo: {','.join(to_addr)}\r\nSubject: {subject}\r\n"
with smtplib.SMTP(host=SMTP_HOST, port=SMTP_PORT) as server:
server.starttls()
server.login(SMTP_USER, SMTP_PASSWORD)
server.sendmail(from_addr, to_addr, msg)
Important note:
When using Gmail, please remember to turn on access for less secure apps

Answer 2

After creating the SMTP connection, you should login: s.login('email', 'password')
EDIT:
Here is the code I have used for years. I used this to send email from a G-Suite account:
server = smtplib.SMTP_SSL(serverAddress, portNumber)
server.ehlo()
server.login(username, password)

Answer 3

Steps:
Try this:
s = smtplib.SMTP('smtp.gmail.com', 587)
s.starttls()
s.ehlo()
s.login(username, password)
If email is ***#gmail.com
Turn this ON: https://myaccount.google.com/lesssecureapps
If email is something else (ex. ***#outlook.com), then no need to do step 2

Answer 4

This works for me!
import smtplib
server_365 = smtplib.SMTP('smtp.office365.com', '587')
server_365.ehlo('mylowercasehost')
server_365.starttls()
server_365.ehlo('mylowercasehost')
Reference: Office365 smtp server does not respond to ehlo() in python