🎯 Advanced Penetration Testing Checklist for HTB, THM & OSCP

A comprehensive penetration testing checklist and methodology for Hack The Box (HTB), TryHackMe (THM), and OSCP-like labs. This guide is designed for cybersecurity learners, ethical hackers, CTF enthusiasts, and OSCP aspirants seeking a structured, repeatable approach to reconnaissance, enumeration, exploitation, privilege escalation, post-exploitation, lateral movement, and objective hunting.

Keywords: penetration testing, CTF, Hack The Box, TryHackMe, OSCP, ethical hacking, cybersecurity, Kali Linux, methodology, checklist.

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🚀 Features

• Step-by-step methodology for penetration testing labs and CTFs
• Covers all phases: Reconnaissance, Vulnerability Assessment, Exploitation, Post-Exploitation, Privilege Escalation, Lateral Movement, and Objective Hunting
• Quick access to essential tools, commands, and troubleshooting tips
• Optimized for Kali Linux, Parrot OS, and other popular pentesting distributions
• Suitable for OSCP, HTB, THM, and similar platforms

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🏁 Getting Started

1. Clone this repository to your local machine:

   git clone https://github.com/yourusername/htb-thm-oscp-checklist.git
   cd htb-thm-oscp-checklist

2. Review the checklist and customize it for your workflow.
3. Follow each phase as you progress through your penetration testing engagement or CTF challenge.

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🛠️ Pre-Engagement Setup

Before starting any penetration test or CTF, ensure your environment is ready:

Environment Preparation

• VPN Connection: Verify HTB/THM VPN connectivity

  ip a | grep tun0  # Check for VPN interface
  ping -c 1 8.8.8.8  # Verify internet connectivity

• Note-Taking Setup: Initialize workspace (Obsidian, CherryTree, Notion)
• Screenshot Tools: Configure Flameshot/Greenshot with hotkeys
• Terminal Setup: Multiple terminals/tmux sessions ready
• Essential Wordlists: Verify SecLists installation and updates
• Proxy Setup: Configure Burp Suite/OWASP ZAP for web testing
• Docker/VM: Ensure isolated testing environment if needed

Initial Information Gathering

• Target Information: Record machine details, IP, difficulty, OS hints
• Platform Tags/Hints: Note all provided hints and tags carefully
• Research Phase: Quick Google search for machine name (if not exam)
• Time Tracking: Set up timer for phase management

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📋 Methodology Phases

After completing initial configuration, follow this systematic approach:

Phase 1: 🔍 Reconnaissance and Enumeration

Phase 2: 🛡️ Vulnerability Assessment

Phase 3: ⚡ Exploitation

Phase 4: 📊 Post-Exploitation

Phase 5: 📈 Privilege Escalation

Phase 6: 🔄 Lateral Movement and Persistence

Phase 7: 🎯 Objective Hunting

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🛠️ Resources and References

• 📚 Toolset and Techniques
• ⚡ Quick Commands
• 🔧 Troubleshooting Tips
• 📝 Conclusion

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This checklist is maintained by cyb3ritic. For more cybersecurity resources, visit my GitHub.

Tags: penetration-testing, oscp, hackthebox, tryhackme, ctf, ethical-hacking, kali-linux, methodology, checklist

Version: 2.1
Last Updated: June 2025
Environment: Kali Linux / HTB/THM Platforms