o365-password-test.poc

#!/usr/bin/env python

from smtplib import SMTP, SMTPAuthenticationError
from getpass import getuser

if __name__ == '__main__':
    server, service_port = "smtp.office365.com", 587
    with SMTP(server, port=service_port) as smtp:
        print('[+] Attempting a login as a bogus user.')
        print(f"[+] connected to server: {server}:{service_port}")
        smtp.starttls()
        smtp.ehlo()
        try:
            user = f"{getuser()}-from-o365-login-proof-of-concept@pdx.edu"
            password = "notarealpass!@#$@#$"
            print(f"[+] Attempting login as: '{user}' with the password '{password}'")
            smtp.login(user, password)
        except SMTPAuthenticationError as err:
            print(f"[!] {err.smtp_code}: {err.smtp_error}")
            smtp_err1 = err.smtp_error
        print(f"\n** Check splunk logs for an attempted login from {user}\n")
    with SMTP(server, port=service_port) as smtp:
        print('[+] Attempting a login as a real user.')
        print(f"[+] connected to server: {server}:{service_port}")
        smtp.starttls()
        smtp.ehlo()
        try:
            user = f"{getuser()}@pdx.edu"
            password = "notarealpass!@#$@#$"
            print(f"[+] Attempting login as: '{user}' with the password '{password}'")
            smtp.login(user, password)
        except SMTPAuthenticationError as err:
            print(f"[!] {err.smtp_code}: {err.smtp_error}")
            if err.smtp_error != smtp_err1:
                print(f"\n** The account '{user}' is configured to disallow basic authentication")