Penetration Testing Practice

Microsoft Entra ID & Azure Penetration Testing

Uncover cloud privilege escalation paths, OAuth application abuse, and Entra ID identity risks.

Identity is the new enterprise perimeter. Riptide Cybersecurity’s Microsoft Entra ID & Azure Penetration Testing assesses how attackers compromise cloud identities, abuse OAuth consents, and traverse from initial access to full Global Administrator or Azure Subscription Owner control.

Real-World Cloud Attack Vectors

We simulate sophisticated cloud-native threat actor tactics:

  • Entra ID & Identity Architecture Attacks: Tenant enumeration, PIM (Privileged Identity Management) privilege escalation, role assignment abuse, and illicit Administrative Unit traversal.
  • Service Principals & App Registrations: Exploiting over-privileged enterprise applications, client secret credential theft, Certificate-based authentication hijacking, and OAuth illicit consent grant attacks.
  • Primary Refresh Token (PRT) & Token Replay: Testing browser token extraction, roadrecon analysis, and token theft across hybrid-joined devices.
  • Conditional Access Policy Bypass: Simulating geographic anomalies, trusted device spoofing, compliant device emulation, and legacy protocol exploitation to circumvent MFA.
  • Azure Infrastructure Traversal: Managed Identity theft from compromised Azure Virtual Machines or Container Apps (AKS), pivoting to Azure Key Vault secrets, storage account access keys, and databases.
  • Hybrid Identity Attack Paths: Assessing Azure AD Connect synchronization account abuse, Password Hash Sync (PHS) / Pass-Through Authentication (PTA) interception, and seamless SSO Golden SAML paths.

Cloud Testing Methodology

  1. Reconnaissance & Tenant Discovery: Passive enumeration of public Entra ID endpoints, federated domains, and exposed cloud workloads.
  2. Assumed Identity & Access Simulation: Gray-box testing simulating a compromised corporate M365 account or low-tier contractor credential.
  3. Graph API & RBAC Path Exploration: Automated and manual traversal using specialized offensive tools (e.g., AzureHound, Stormspotter, ROADtools) to identify non-obvious permission chains.
  4. Data Exfiltration & Persistent Access Testing: Validating whether malicious automation could establish persistent federated identity backdoors or exfiltrate sensitive cloud storage data without triggering Microsoft Defender for Cloud alerts.

Deliverables & Hardening Playbooks

  • Visual Cloud Attack Path Graph: Step-by-step diagram showing the exact sequence of role assignments, Managed Identities, and App Registrations chained together during exploitation.
  • Conditional Access Hardening Matrix: Actionable policy blueprints to eliminate device and location bypasses.
  • Privileged Access Workstation (PAW) Guidance: Hardening architectures to isolate Global Admin and Cloud Admin credentials from routine workstation exposure.

Committed to Your Success

All assessments include a complimentary 90-day retest window for Critical and High severity findings, along with updated formal attestation reporting upon patch confirmation.

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