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Sherlocked Security – AI-Powered Cybersecurity & Penetration TestingSherlocked Security – AI-Powered Cybersecurity & Penetration Testing
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  • About Us
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    • Secure Development & DevSecOps
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  • Endpoint Evasion & Obfuscation Testing,md
Red Teaming & Adversary Simulation

Endpoint Evasion & Obfuscation Testing,md

  • May 8, 2025
  • 0

Sherlocked Security – Endpoint Evasion & Obfuscation Testing

Test Your Endpoint Defenses by Bypassing Security Controls with Advanced Evasion Techniques


1. Statement of Work (SOW)

Service Name: Endpoint Evasion & Obfuscation Testing
Client Type: Enterprises, MSSPs, Managed Security Providers, Government, Critical Infrastructure
Service Model: Manual Penetration Testing with Evasion Tools
Compliance Coverage: NIST 800-53, CIS Controls, SOC 2, ISO 27001

Testing Types:

  • Evasion Techniques Simulation
  • Bypass EDR/AV/NGAV Detection
  • Endpoint Detection & Response (EDR) Evasion
  • Obfuscation & Encryption Methods
  • Custom Payload Creation and Delivery

2. Our Approach

[Test Environment Setup] → [Payload Development] → [Evasion Technique Selection] → [Test Execution] → [Detection Evasion Testing] → [Obfuscation Validation] → [Results Analysis] → [Remediation Planning]


3. Methodology

[Kickoff & Access Approval] → [Threat Emulation Plan] → [Test Selection (AV/EDR Specific)] → [Payload Development & Testing] → [Execution & Detection Mapping] → [Reporting & Retesting]


4. Deliverables to the Client

  1. Evasion Test Plan: Detailed emulation of attack techniques
  2. Payload Development Logs: Obfuscation and evasion methods employed
  3. Detection Testing Report: Identification of EDR/AV evasion effectiveness
  4. Remediation Plan: Actionable recommendations for improving endpoint defenses
  5. Executive Summary: Simplified report for higher management
  6. Detection Gap Analysis: Analysis of detection blind spots and evasion success
  7. Retesting & Certification: Validation of defensive improvements

5. What We Need from You (Client Requirements)

  • Access to a testing environment or staging infrastructure
  • Endpoint Protection Solution details (AV/EDR/NGAV configuration)
  • Sample of existing endpoint telemetry/logging data
  • SOC/IT/Infra contact for troubleshooting
  • Approval to test on live endpoints (if applicable)
  • Access to threat intel or existing attack vectors used in the organization

6. Tools & Technology Stack

  • Cobalt Strike / Brute Ratel
  • Metasploit Framework
  • Empire (PowerShell-based attack framework)
  • Custom Evasion Payloads
  • Obfuscation Tools (Shellter, Veil-Evasion)
  • Fileless payload delivery tools
  • EDR/AV Analysis & Bypass Scripts
  • Custom Tools / Scripts

7. Engagement Lifecycle

1. Initial Discovery Call → 2. Test Planning & Setup → 3. Evasion Simulation (1-2 Weeks) → 4. Detection Mapping & Analysis → 5. Draft Report + SOC Review → 6. Final Report + Remediation Plan → 7. Retesting & Final Certification


8. Why Sherlocked Security?

Feature Sherlocked Advantage
Advanced Evasion Techniques Test evasion against next-gen AV/EDR systems
Custom Payload Development Tailored payloads that bypass multiple defenses
Realistic Attack Simulation Simulate real-world techniques for more accurate defense validation
Detection & Evasion Mapping Real-time visibility into your endpoint defenses
Ongoing Support Expert remediation advice and retesting at a reduced cost
Retesting Certification Final security assessment post-remediation

9. Real-World Case Studies

AV Evasion for Financial Institution

Objective: Test the evasion of financial institution’s endpoint defenses using advanced attack techniques.
Outcome: Successfully bypassed two major AV systems and maintained stealth on endpoints for over 72 hours.
Fix: Implemented additional heuristic analysis and behavioral detection rules, improving detection efficacy by 30%.

EDR Evasion for Healthcare Provider

Client: National healthcare service provider
Scenario: Simulated targeted attack bypassing the EDR layer with custom payloads.
Findings: EDR failed to detect fileless execution techniques.
Result: EDR configuration updated to detect PowerShell-based attacks, additional monitoring implemented.


10. SOP – Standard Operating Procedure

  1. Kickoff call and review of endpoint security controls
  2. Define scope (AV/EDR/NGAV targets)
  3. Payload development and customization for specific EDR systems
  4. Test evasion techniques against security controls
  5. Analyze detection success rates and timing
  6. Generate report with findings and improvement suggestions
  7. Collaborate with SOC for feedback and gap identification
  8. Retest and validate improvements
  9. Deliver final security certificate post-fix

11. Evasion Testing Checklist

1. AV/EDR/NGAV Bypass

  • Test signature-based detection avoidance (T1068)
  • Test heuristics-based detection avoidance (T1083)
  • Evasion via fileless malware techniques (PowerShell, WMI, etc.)
  • Obfuscate shellcode using various tools (Veil-Evasion, Shellter)
  • Reverse engineer or modify binaries to avoid detection
  • Test AV/EDR’s response to custom payloads

2. Payload Development & Delivery

  • Craft custom payloads to avoid detection (T1203, T1106)
  • Test bypass techniques for different file types (executable, DLL, script)
  • Evaluate network-based delivery methods (HTTP, DNS tunneling)
  • Create encrypted payloads and test decryption bypass
  • Ensure payload persistence across reboots (T1100)

3. Endpoint Evasion Techniques

  • Use living-off-the-land binaries (LOLbins)
  • Modify process memory (process injection)
  • Test evasive techniques against native security controls
  • Evade PowerShell detection using encoded scripts
  • Use fileless payloads to maintain stealth
  • Attempt registry and scheduled task persistence (T1053, T1071)

4. Detection & Response Testing

  • Analyze endpoint detection logs for successful bypass events
  • Validate SOC’s ability to correlate and detect evasion techniques
  • Test detection systems’ response time for various evasion methods
  • Document failed detection events and gaps
  • Simulate lateral movement while maintaining evasion techniques

5. Reporting & Remediation

  • Detail each evasion method and success rate
  • Map techniques to MITRE ATT&CK framework (T1070, T1059)
  • Provide remediation steps for AV/EDR bypass
  • Recommend detection rule tuning for evasion-proofing
  • Retest after remediation and certification

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