Keys to the Kingdom: Inside the Black Hat 2025 Authentication Breach


Keys to the Kingdom: Inside the Black Hat 2025 Authentication Breach

Imagine two locks one securing legacy on-prem systems, another protecting cloud infrastructure. At Black Hat 2025, researchers showed how both can be silently picked, allowing attackers to forge tokens, impersonate users, and bypass MFA entirely. As a part-time penetration tester, that moment hit like a gut punch: even trusted identity foundations aren’t safe. This revelation underscores a crucial truth: in modern networks, defense must assume that every layer can be breached and testing must be ready to detect it.

Endpoint to Entra: How Low-Privilege Accounts Can Become Admins

Mollema demonstrated a method to convert a low-privilege cloud-only account into a hybrid admin via Entra ID soft matching granting full Tenant access undetected. Attackers exploited weakened syncing logic between AD and Entra ID, breaking the trusted boundary.

Seamless SSO & SAML Forgery: Core Identity Trust Abused

The techniques extend into leveraging Exchange hybrid certificates and seamless SSO for forging S2S tokens. These unsigned tokens exploit trusted delegation claims, enabling complete impersonation of user identities without audit trails or triggering Conditional Access policies.

Legacy Protocols: The Silent MFA Killer

A separate campaign exploited Entra ID’s legacy authentication protocols like BAV2ROPC, SMTP AUTH, and IMAP4 to bypass MFA and Conditional Access entirely. These deprecated endpoints, still enabled in many environments for compatibility, enabled silent credential spraying and token issuance.

Why Hybrid Identity is Penetration Testing’s New Frontier

These vulnerabilities highlight that hybrid identity systems-Active Directory syncing with cloud identity contain structural risks. The identity datastore is now a critical attack surface often overlooked in traditional tests focused on perimeter or application logic.

Penetration Testing Scenarios to Simulate AD-Entra Attacks

  • Test soft matching logic: Create overlapping cloud-only / AD accounts to test covert privilege escalation.

  • Forge tokens via hybrid certificates: Simulate S2S impersonation without logs.

  • Assess legacy auth endpoints: Deploy BAV2ROPC-based access attempts to validate MFA bypass.

  • API policy fuzzing: Alter Graph API policy settings to evaluate perimeter integrity.

Supply Chain Implications: Sync Tools As Attack Vectors

Microsoft Entra ID Connect servers become potent attack vectors if compromised, they can export sync certificates and private keys, enabling token forgery and tenant-wide takeover.

Defense Tools and Tactical Simulations from Black Hat Arsenal

Semperis unveiled tools like SAMLSmith and EntraGoat, designed to simulate SAML response forging and vulnerable Entra ID environments. These solutions let red and blue teams practice against real-world identity threats in hands-on settings.

 Identity Bypass is Cyber Warfare’s Next Expedition

State-backed actors and ransomware groups see hybrid identity flaws as powerful leverage points. These bypasses offer undetectable access ideal for espionage, persistent ransomware staging, or supply chain infiltration.

Expert Insight

James Knight, Senior Principal at Digital Warfare.“Identity infrastructure is a chain if identity synchronization or SSO logic is weak, the attacker’s path is linear. Penetration testing must include hybrid identity and trust boundary checks.” 

Immediate Defensive Measures for Hybrid Identity

ActionPurpose
Audit syncing servers for key extractionDetect misuse of Entra ID Connect credentials
Enforce hardware-bound key storagePrevent export of critical SSO or certificate keys
Harden legacy auth policiesDisable BAV2ROPC and legacy protocols
Use Arsenal tools like SAMLSmithTrain detection against token forgery
Monitor Graph API and synchronization logsDiscover tampering or anonymized escalation paths

Final Thought: Identity Is Not a Roadblock, It’s the Highway

AD–Entra ID bypasses demonstrate that identity systems are no longer safeguards they're the pathway. To pen-test in 2025 means testing identity end-to-end, from on-prem endpoints to cloud policy enforcement.

Call to Action

  • Include hybrid identity bypass tests in red-team playbooks

  • Train blue teams using Arsenal tools (EntraGoat, SAMLSmith)

  • Exchange insights with peers on identity vector detection

  • Leverage  methods to stress-test cloud identity resilience

Because when identity systems fail, the attacker is already inside or already gone

Comments

Post a Comment

Popular posts from this blog

When Trust Becomes the Threat: A Pen Tester’s Breakdown of the BCNYS Data Leak

When Trust Becomes the Threat: A Pen Tester’s Breakdown of the BCNYS Data Leak It starts the way most breaches do-quietly. No alarms. No fanfare. Just a small foothold in a system trusted by thousands. For nearly six months, attackers moved silently through the digital corridors of the Business Council of New York State, siphoning off sensitive data from over 47,000 individuals- names, Social Security numbers, bank details, even health insurance records-all exfiltrated without tripping a single wire. As a penetration tester and independent blogger, this breach doesn’t just raise red flags-it screams systemic failure. This wasn’t a brute-force attack or a flashy zero-day exploit. It was a supply chain compromise , subtle and lethal. The kind of vulnerability we see every day in assessments, buried under layers of trust and assumption. It’s a hard reminder: in modern cybersecurity, your weakest link is rarely your firewall-it's your vendor. Why This Breach Resonates with Penetration...
Read more

Hacking the Matrix: A Pen Tester’s Dispatch from June 2, 2025’s Cyber Battleground

  Hacking the Matrix: A Pen Tester’s Dispatch from June 2, 2025’s Cyber Battleground What’s up, cyber renegades? It’s your friendly neighborhood pen tester and indie blogger, back with a fresh dive into the cybersecurity chaos of June 2, 2025. By day, I’m slipping through digital backdoors (ethically, of course); by night, I’m glued to news feeds, decoding the latest threats like a hacker on a mission. Today’s digital landscape is a wild ride—AI-driven cyberattacks evolving like rogue algorithms, state-sponsored espionage playing high-stakes chess, ransomware gangs holding systems hostage, and supply chain vulnerabilities lurking like hidden exploits. With a terminal humming and a playlist blasting, I’m here to unpack the latest cybersecurity events with a pen tester’s edge, gritty anecdotes, and practical tips to keep your skills locked and loaded. Let’s crack the code and dive into the fray. State-Sponsored Cyber Siege: Scattered Spider’s Transatlantic Hustle I’m scrolling CBS...
Read more

Cracking Today’s Cyber Chaos

  Cracking Today’s Cyber Chaos: June 16, 2025, Cybersecurity Events. Yo, hackers and cyber nerds! It’s your favorite part-time pen tester and full-time cybersecurity obsessive, back to unpack the digital dumpster fire that is June 16, 2025. As someone who spends their days breaking into systems (ethically, of course) and their nights chasing the latest threat intel, I’m pumped to dive into today’s freshest cybersecurity events. From Chinese APTs exploiting zero-days to ransomware gangs flexing on Linux, AI-powered malware dodging defenses, and supply chain attacks hitting npm, the internet is popping off. So, boot up your Kali Linux, crack open a Monster Energy, and let’s dissect these threats with a hacker’s mindset—complete with pen testing tips to keep you sharp. Today’s Threat Landscape: June 16, 2025, in Focus The cyber world moves fast, and June 16 is no exception. My feeds are blowing up with breaking news about targeted attacks, sneaky malware, and scams that make my pen...
Read more