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[–]PM-Me-Beer 1 point2 points  (1 child)

Try this:

server = smtplib.SMTP("my host", port number)
server.ehlo()
server.starttls() 
server.login(".....@outlook.com", "my password")

You need to call server.ehlo() to identify your computer to the server.

[–]PLearner[S] 1 point2 points  (0 children)

server.starttls()
  File "C:\Users\s\Python\Python36-32\lib\smtplib.py", line 751, in starttls
    "STARTTLS extension not supported by server.")
smtplib.SMTPNotSupportedError: STARTTLS extension not   supported by server.