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noahfranklinnoahfranklin/gideon/skills/entra-cloud-pentest/SKILL.md

entra-cloud-pentest

Skill2 starsChanged 47 days agoMITView on GitHub

Use when testing Microsoft Entra ID (Azure AD) and Microsoft 365 identity security — tenant/user enumeration, authentication attacks (password spray, MFA gaps, legacy auth), conditional-access bypass, OAuth/app-consent abuse, privileged-role and Graph API abuse, and hybrid AD-to-cloud (and cloud-to-AD) attack paths. Maps to MITRE ATT&CK, with detection and remediation. Authorized engagements only.

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SKILL.md

Entra ID (Azure AD) & M365 Identity Testing

Assessment of cloud identity — the modern crown jewels. Covers Entra ID, M365, and hybrid attack paths bridging on-prem AD and the cloud. Mapped to MITRE ATT&CK.

0. Authorization gate

  • Written authorization from the tenant owner (cloud provider ToS also apply).
  • Scope: tenant, in-scope identities/apps, allowed auth testing (spray limits).
  • Coordination with the SOC (identity attacks generate alerts).

1. Enumeration

  • Tenant existence/details, federation/managed domains, user enumeration via auth responses, guest accounts.
  • Enumerate roles, service principals, enterprise apps, app registrations, and API permissions.

2. Authentication attacks

  • Password spray (lockout- and lockout-alert-aware), against exposed auth endpoints.
  • Legacy auth protocols that bypass modern controls / MFA.
  • MFA gaps & fatigue: accounts without MFA, weak methods, push-fatigue susceptibility (test per RoE).
  • Device-code & consent phishing: OAuth device-code flow abuse and illicit consent as MFA-aware phishing paths (test per RoE; coordinate with social-engineering).
  • Token / Primary Refresh Token (PRT) theft & replay: stolen tokens that sidestep re-authentication — assess token-protection posture (conditional-access token binding, sign-in risk).
  • Fix: disable legacy auth, enforce phishing-resistant MFA, smart lockout, block-legacy conditional access.

3. Conditional Access (CA) review & bypass

  • Enumerate CA policies; look for gaps: excluded apps/users, device/location loopholes, report-only policies, missing coverage.
  • Fix: close exclusions, require compliant devices + MFA broadly, remove report-only gaps.

4. OAuth / application & consent abuse

  • Illicit consent grants, over-privileged app registrations, dangerous Graph permissions, credential/secret exposure on service principals.
  • Fix: restrict user consent, review app permissions (least privilege), monitor consent grants, rotate SP secrets.

5. Privilege escalation & Graph abuse

  • Escalation via role assignments, service principals with high privilege, group-based role grants, and Microsoft Graph API abuse.
  • Fix: PIM (just-in-time roles), least-privilege role model, monitor privileged role/SP changes.

6. Hybrid attack paths (the high-value part)

  • On-prem → cloud: connect-sync account abuse, Seamless SSO/PRT abuse, federation (token-signing) trust abuse.
  • Cloud → on-prem: management endpoints (Intune/config) to run code on enrolled/hybrid devices.
  • Correlate with active-directory-pentest — hybrid paths are prime vuln-chaining territory.
  • Fix: protect sync/federation servers as tier-0, restrict privileged identities, segment management planes.

7. Tooling

AADInternals, ROADtools/roadrecon, GraphRunner, MSOLSpray (spray, lockout-aware), Microsoft Graph queries. Follow RoE and provider ToS.

8. Reporting

Present as identity attack paths with detection guidance; emphasize MFA/CA hardening and tier-0 protection of sync/federation. Checklist: references/entra-checklist.md.

<sub>© 2026 noahfranklin · Part of the Gideon security suite · MIT License · Original work.</sub>

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