SPNEGO to SQL: How Microsoft’s July Patch Cycle Is a Goldmine for Penetration Testers

 

SPNEGO to SQL: How Microsoft’s July Patch Cycle Is a Goldmine for Penetration Testers

On July 15, 2025, Microsoft issued a massive Patch Tuesday update, closing out 130+ vulnerabilities, including newly disclosed zero-days and critical RCE threats. This deep-dive explores the pen testing relevance behind these fixes covering AI-driven exploitation, nation-state vectors, ransomware resilience, and supply chain integrity. Let’s break down what to test, how to test it, and why it matters today.

Massive Fix Rollout: 130+ Vulnerabilities Patched

Microsoft’s July Patch Tuesday addressed over 130 CVEs, including one publicly disclosed zero-day (CVE‑2025‑49719) in SQL Server and several RCE fixes in core components like SPNEGO, SharePoint, Windows Connected Devices Platform, and BitLocker.

Pen Testing Insight

  • Prioritize SQL Server and SPNEGO RCEs in test scope.

  • Include Office Preview Pane flaws in social engineering scenarios.

  • Scan BitLocker bypass vectors as part of disk encryption assessments.

CVE‑2025‑49719: The SQL Server Info Leak

This publicly disclosed zero-day allowed unauthenticated attackers to leak uninitialized memory over the network.

Pen Testing Insight

  • Simulate info-leak via crafted SQL queries.

  • Test for leaked authentication tokens or connection strings.

  • Verify use of OLE DB Drivers 18/19 across environments.

SPNEGO NEGOEX RCE: A Wormable Threat

CVE‑2025‑47981, a heap-based buffer overflow in SPNEGO negotiation, carries a 9.8 CVSS—making it a potential wormable exploit.

Pen Testing Insight

  • Inject large SPNEGO negotiation payloads using custom scripts.

  • Monitor detection capability of EDR/IDS systems during exploit attempts.

  • Assess lateral spread across unmanaged Windows domains.

Office & SharePoint RCE: User-Triggered Hazards

Critical vulnerabilities in Office (use-after-free, OOB reads) and SharePoint allow RCE via malicious documents or HTTP requests.

Pen Testing Insight

  • Build .docx with RCE vectors and test Preview Pane exploits.

  • Audit SharePoint for unauthenticated code injection.

  • Verify content filtering and patch compliance on servers.

Windows Connected Devices and KDC Proxy Flaws

CVE‑2025‑49724 impacts Nearby Share service; CVE‑2025‑49735 affects KDC proxy—both sound attackers can exploit remotely.

Pen Testing Insight

  • Test crafted incoming packets with Nearby Share enabled.

  • Simulate KDC spoofing in hybrid-environment pen tests.

  • Probe elevated domain privilege escalations via Kerberos bypass.

BitLocker Bypass Vulnerabilities

Microsoft patched 5 BitLocker bypass issues, highlighting concerns in hardware and storage management subsystems.

Pen Testing Insight

  • Attempt bypass via firmware-level or driver-mode exploits.

  • Simulate physical access tests using pre-boot tools.

  • Confirm TPM security and OS updates mitigate bypass methods.

AI-Powered Exploitation & Defense

This patch cycle marks increasing AI dual-use: while attackers automate exploit creation, defenders deploy agents like Google’s Big Sleep to spot zero-days preemptively.

Pen Testing Insight

  • Use AI fuzzing (FuzzGPT, DeepFuzz) for SPNEGO and Office protocols.

  • Simulate adversarial AI payloads in automated pen testing frameworks.

  • Compare traditional vs. AI-augmented vulnerability discovery results.

State-Backed Attacks & Zero-Days

Microsoft’s RCE patches align with known nation-state tactics—particularly SQL Server and SPNEGO modes observed in APT intrusions.

Pen Testing Insight

  • Include SQL Server in supply-chain attacks.

  • Simulate APT techniques focusing on stealthy domain authentication bypass.

  • Audit for unsigned logs and evidence of C2 communication patterns.

Ransomware Prevention Through Pen Testing

Resetting backups and ransomware attackers often exploit vulnerabilities like those patched, aiming for encryption post-exploit.

Pen Testing Insight

  • Deploy simulated ransomware post-exploit for recovery testing.

  • Test data exfil routines via SQL Server info leaks.

  • Validate backup integrity and detection systems under pressure.

Supply Chain Risk: Dependencies & CVEs

The update also covered vulnerabilities in third-party tools (Chromium Edge, AMD, Visual Studio), underscoring supply chain exposure.

Pen Testing Insight

  • Map Edge and dev tool use in test environments.

  • Audit CI/CD toolchains for outdated dependencies.

  • Inject mock vulnerable binaries to test detection and build integrity checks.

Pen Testing Toolkit Updates

ThreatTools & Techniques
SQL Server Info LeakMetasploit, SQLmap, custom scripts
SPNEGO RCEPython SPNEGO fuzzer + EDR trickle
Office RCEBurp collaborator, Office macros, exploit chaining
SharePoint InjectionSPIDE, HTTP-targeted payloads
BitLocker bypassPre-boot tools, secure firmware settings
AI fuzzingFuzzGPT, DeepFuzz on SPNEGO, Office formats
Backup resilience testSimulated encryption + restore workflows
Supply chain exploitSBOM, container fuzzing, binary substitution

Human Element & Social Engineering

Office and SharePoint flaws rely on social engineering to trigger. Employees remain key targets in delivering malicious documents.

Pen Testing Insight

  • Run phishing campaigns with document lure.

  • Embed macros or payloads to test detection.

  • Test user response and reporting within 24 hours.

Compliance Checklists

  • CISA KEV: Rapid patching of SPNEGO, SQL Server, KDC proxies.

  • NIST SP 800-115: Include patched systems in pen testing scope.

  • GDPR: Resolve data leaks from SQL server RCE tests.

  • Supply Chain: Regular dependency and Edge update audits.

  • AI Governance: Trytech AI-fuzzing in compliance reports.

Expert Insight

James Knight, Senior Principal at Digital Warfare, said: “Patch Tuesday isn’t just volume—it highlights attack vectors we must simulate. From SPNEGO to SQL leaks, pen testing must dive into service-level threats that attackers will weaponize first.”

Conclusion & Call to Action

July 15’s patch cycle is more than reactive-it’s a roadmap for proactive testing. From SQL servers to domain authentication, from Office to firmware, ethical hackers must simulate today’s threats before adversaries do. Ramp up your pen testing methodology to include AI abuse and state-level persistence tactics. Test deeper. Remediate faster. Stay ahead.

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