The Foundation: Rules of Engagement

Every successful pentest begins not with a tool, but with a conversation. Before a single packet is sent, establishing clear Rules of Engagement (RoE) is paramount. This document is the contract that governs the entire assessment, defining scope, limitations, and communication protocols. It protects both the client and the tester, ensuring that the assessment is effective, ethical, and free of surprises.

  • Scope: What domains, applications, and APIs are in-scope?
  • Testing windows: When is testing allowed? Are there blackout periods?
  • Contact points: Who to notify in case of critical findings or emergencies?
  • Legal & compliance: Are there data residency or privacy requirements?
Green code on a black screen

Methodology: Step-by-Step Approach

  1. Reconnaissance & Information Gathering
    • Passive: WHOIS, DNS, certificate transparency logs, Google dorking, public breach data, subdomain enumeration (e.g., amass, subfinder).
    • Active: Port scanning (nmap), directory brute-forcing (ffuf, dirsearch), endpoint discovery, analyzing robots.txt and sitemap.xml.
  2. Mapping the Application
    • Manual browsing and spidering (Burp Suite, OWASP ZAP) to understand functionality and user flows.
    • Identifying authentication, session management, and access control mechanisms.
  3. Vulnerability Analysis & Exploitation
    • Testing for OWASP Top 10: SQLi, XSS, CSRF, IDOR, SSRF, file upload issues, etc.
    • Business logic testing: Unintended workflows, privilege escalation, bypasses.
    • Automated scanning (Burp Suite Scanner, Nuclei) and manual validation.
    • Exploitation: Demonstrating impact safely, e.g., extracting sample data, privilege escalation, or session hijacking.
  4. Post-Exploitation & Cleanup
    • Documenting all actions for reproducibility.
    • Ensuring no test accounts or payloads are left behind.

Tooling: My Go-To Stack

  • Burp Suite Pro – Interception, scanning, repeater, intruder, and extensions.
  • OWASP ZAP – Free alternative for proxying and scanning.
  • ffuf, dirsearch – Fast content discovery and brute-forcing.
  • amass, subfinder – Subdomain enumeration.
  • Nuclei – Fast, template-based vulnerability scanning.
  • Custom scripts – For automation, parsing, and edge-case testing (Python, Bash).
  • Browser DevTools – For manual analysis, JavaScript debugging, and CSP review.

Reporting: Delivering Value

  • Clear structure: Executive summary, methodology, findings (with risk ratings), and actionable remediation steps.
  • Evidence: Screenshots, request/response pairs, and PoC scripts where appropriate.
  • Reproducibility: Step-by-step instructions for each finding.
  • Prioritization: Focus on business impact, not just technical severity.
  • Debrief: Offer a call or meeting to walk through the report and answer questions.

Want to secure your application?

Let's work together to identify and remediate vulnerabilities before they become a problem.

Get in Touch

Final Thoughts

Effective black-box web application assessments require a blend of structured methodology, the right tools, and clear communication. By focusing on both technical and business risks, and delivering actionable, well-documented reports, you help clients not only fix vulnerabilities but also improve their overall security posture.