User enumeration for O365 users

office_enum.py

# -*- coding: utf-8 -*-
from __future__ import unicode_literals

import logging
from ipaddress import IPv4Address
from random import getrandbits
import requests

logger = logging.getLogger()



def generate_random_ip():
    bits = getrandbits(32)
    addr = IPv4Address(bits)
    return str(addr)


def check_office(domain):
    headers = {
        "X-Forwarded-For": generate_random_ip(),
        "User-Agent": "Mozilla/5.0 (Windows NT 10.0; Win64; x64; "
        "rv:75.0) Gecko/20100101 Firefox/75.0",
    }

    try:
        r = requests.get(
            "https://outlook.office365.com/autodiscover/autodiscover.json/v1.0/x@{}?"
            "Protocol=Autodiscoverv1".format(domain),
            headers=headers,
            timeout=10,
        )
        try:
            x = r.json()
            if "Protocol" in x:
                return True
        except:
            pass
        if "outlook.office365.com" in r.url:
            return True
        return False
    except Exception as e:
        logger.error(e)
        return False


def enum_office(email):
    headers = {
        "X-Forwarded-For": generate_random_ip(),
        "User-Agent": "Mozilla/5.0 (Windows NT 10.0; Win64; x64; "
        "rv:75.0) Gecko/20100101 Firefox/75.0",
    }
    # request 1

    random_password = generate_random_ip()
    try:
        requests.get(
            "https://outlook.office365.com/autodiscover/autodiscover.json/v1.0/{}?"
            "Protocol=Autodiscoverv1".format(email),
            allow_redirects=False,
            headers=headers,
            auth=(email, random_password),
            timeout=20,
        )
    except Exception as e:
        logger.error(e)

    # request 2
    try:
        r2 = requests.get(
            "https://outlook.office365.com/autodiscover/autodiscover.json/v1.0/{}?"
            "Protocol=Autodiscoverv1".format(email),
            allow_redirects=False,
            headers=headers,
            auth=(email, random_password),
            timeout=20,
        )
    except Exception as e:
        r2 = None
        logger.error(e)

    # check if r1 and r2 are made and r2 

    if r2:
        resp_headers = r2.headers
        live_id_basic_auth = resp_headers.get("X-AutoDiscovery-Error", None)
        if live_id_basic_auth:
            if "RepeatedBadPassword" in live_id_basic_auth:
                print(f"valid email {email}")
                return email
    print(f"Not a valid email {email}")
    return False

enum_office("email to check")