Pentesting & Red Teaming: Stories & Guides

TL;DR

This guide shows you how to document and share your Pentesting and Red Team engagements effectively, covering planning, execution, reporting, and turning those experiences into valuable blog posts or stories. We’ll focus on practical steps for both technical details and broader lessons learned.

1. Planning Your Documentation

1. Define the Audience: Who are you writing for? Technical peers? Management? Beginners? This shapes your level of detail.
2. Scope & Objectives: Clearly outline what was tested/engaged, and the goals (e.g., identify vulnerabilities, simulate an attacker).
3. Confidentiality: Crucially, remove any sensitive data before sharing! This includes IP addresses, usernames, passwords, internal system names, etc. Use placeholders or anonymized examples.
4. Legal Review: If you’re publishing externally, get legal approval to ensure compliance with NDAs and client agreements.

2. Documenting the Engagement (During Execution)

Real-time documentation is vital. Don’t rely on memory.

1. Note Taking: Use a dedicated tool like Obsidian, CherryTree, or even a simple text editor.
2. Command History: Copy and paste important commands with their output.

   ls -la /sensitive/directory

3. Screenshots & Recordings: Capture evidence of vulnerabilities, exploits, and key actions. Be mindful of sensitive information in screenshots – redact as needed.
4. Timeline: Create a chronological record of events. This is essential for storytelling later. Include timestamps.
5. Tools Used: List all tools employed (e.g., Nmap, Metasploit, Burp Suite) and their versions.

3. Reporting – The Core Technical Document

1. Executive Summary: A non-technical overview for management. Focus on risk and impact.
2. Technical Details: This is the meat of the report.
   • Vulnerability Descriptions: Explain each vulnerability clearly, including its CVSS score (if applicable).
   • Proof of Concept (PoC): Demonstrate how the vulnerability was exploited. Include steps and code snippets where appropriate.

     python exploit.py -t target_ip -p 80

   • Remediation Recommendations: Provide specific, actionable advice to fix the vulnerabilities.
3. Supporting Evidence: Include screenshots, logs, and command outputs.
4. Report Format: Use a professional format (PDF is common). Tools like ReportPortal can help automate this.

4. Turning Reports into Blog Posts/Stories

Transform technical reports into engaging content.

1. Identify the Narrative: What’s the interesting story? Was it a particularly challenging engagement? A novel exploit technique?
2. Simplify Technical Jargon: Explain complex concepts in plain language. Use analogies and visuals.
3. Focus on Lessons Learned: Highlight what you (or others) learned from the engagement. This is valuable for the community.
4. Anonymize Data: Double-check that all sensitive information has been removed.
5. Structure Your Post:
   • Introduction: Set the scene and explain the context.
   • Reconnaissance: Describe how you gathered information about the target.
   • Exploitation: Detail the steps taken to exploit vulnerabilities (simplified).
   • Post-Exploitation: Explain what you did after gaining access.
   • Conclusion: Summarize the key findings and lessons learned.

5. Platforms for Sharing

• Personal Blog: Gives you full control over content and branding.
• Medium: Easy to use and has a built-in audience.
• Security Blogs (e.g., Hack The Box Blog): Reach a targeted security community.
• Conference Talks/Writeups: Share your knowledge at industry events.