You want to just say EHLO before running straight into STARTTLS:
server = smtplib.SMTP('smtp.gmail.com:587')
Additionally, you should make From:, To: and Subject: message headers, isolated from the message body by a clear line and use CRLF as EOL markers.
msg = "\r\n".join([
"From: [email protected]",
"To: [email protected]",
"Subject: Just a message",
"Why, oh why"
With the goal for this to work you want to enable the "allow less secure applications" choice in your Gmail account configuration. Else you will get a "basic security alert" when Gmail identifies that a non-Google application is attempting to login to your account.
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