For my machine, after logging in the windows system, the outlook logon automatically with Anonymous Authentication.
The outlook connects to Microsoft Exchange using HTTP, and connects using SSL only.
The Microsoft Exchange server is
code@ms.exchange.server
The principal name in the certificate is known when connecting to proxy servers.
Header:email.server.sample
The URL to connect to my proxy server for Exchange is known.
https://email.server.sample
"Negotiate Authentication" is used when connecting to the proxy server for Exchange.
Now, the question is, how can python sends out the email with this kind of situation?