Cyber Security Learning Roadmap for Red Teaming and Penetesting.md

Complete Cybersecurity Learning Roadmap 2025

Focused on Red Teaming, Penetration Testing & Script Development

🎯 Phase 1: Essential Foundations (2-3 months)

Core Technical Skills:

• Linux Mastery: Command line, bash scripting, system administration, file permissions
• Networking Deep Dive: TCP/IP stack, subnetting, routing, DNS, HTTP/HTTPS protocols
• Windows Fundamentals: PowerShell, Active Directory basics, Windows security model

Programming Priority:

1. Python (Top Priority) - Automation, exploit development, tool creation
2. Bash - Linux automation and scripting
3. PowerShell - Windows red teaming operations
4. Basic C/C++ - Understanding exploit development

Essential Tools Introduction:

• Nmap - Network reconnaissance
• Wireshark - Traffic analysis
• Burp Suite - Web application testing
• Metasploit - Exploitation framework

🔥 Phase 2: Penetration Testing Core (3-4 months)

Web Application Security:

• OWASP Top 10 vulnerabilities (SQLi, XSS, CSRF, etc.)
• Manual exploitation techniques
• Web application enumeration
• Session management attacks

Network Penetration Testing:

• Vulnerability assessment with Nessus/OpenVAS
• Manual verification of vulnerabilities
• Privilege escalation (Windows & Linux)
• Lateral movement techniques

Key Tools Mastery:

• Metasploit Framework - Complete mastery
• SQLMap - Database exploitation
• Burp Suite Professional - Web testing
• Nessus/OpenVAS - Vulnerability scanning

First Certification Target:

• eJPT (eLearnSecurity Junior Penetration Tester) - Practical, hands-on approach
• Alternative: OSCP if you're confident in your skills

⚔️ Phase 3: Red Team Operations (4-6 months)

Advanced Exploitation:

• Buffer overflow exploitation
• Custom payload development
• Antivirus/EDR evasion techniques
• Post-exploitation persistence

Active Directory Attacks:

• Kerberoasting and AS-REP roasting
• Golden/Silver ticket attacks
• Pass-the-hash/Pass-the-ticket
• BloodHound for AD enumeration

Red Team Infrastructure:

• Cobalt Strike operations
• Custom C2 frameworks
• Traffic obfuscation
• Team collaboration tools

Advanced Tools:

• BloodHound & SharpHound - AD mapping
• Impacket Suite - Network protocols exploitation
• CrackMapExec - Network enumeration
• Empire/Starkiller - Post-exploitation

Target Certifications:

• CRTP (Certified Red Team Professional) - AD focused
• CRTO (Certified Red Team Operator) - Advanced red teaming
• OSEP - Advanced penetration testing

💻 Phase 4: Advanced Scripting & Automation (3-4 months)

Custom Tool Development:

• Reconnaissance automation scripts
• Custom exploit development
• Payload generation and obfuscation
• Report generation automation

Advanced Programming:

• Go - Modern tool development
• C# - Windows exploitation
• Assembly - Low-level exploit development
• JavaScript - Client-side attacks

Script Categories to Master:

• Network scanning automation
• Web application testing scripts
• Post-exploitation utilities
• Data exfiltration tools

🎖️ Phase 5: Specialized Domains (3-6 months each)

Choose Your Specialization:

Option A: Advanced Red Teaming

• Social engineering campaigns
• Physical security testing
• Advanced persistent threat simulation
• Custom malware development

Option B: Cloud Security (High Demand)

• AWS/Azure/GCP security testing
• Container security (Docker/Kubernetes)
• Serverless exploitation
• Cloud-native tool exploitation

Option C: Mobile Security

• Android/iOS application testing
• Mobile device exploitation
• API security testing

📚 Recommended Learning Resources

Hands-On Platforms:

1. Hack The Box - Advanced scenarios
2. TryHackMe - Structured learning paths
3. PentesterLab - Web application focus
4. AttackDefense - Cloud and AD labs

Books:

• "The Web Application Hacker's Handbook"
• "Red Team Field Manual"
• "Linux Basics for Hackers" by OccupyTheWeb
• "Black Hat Python" by Justin Seitz

YouTube Channels:

• IppSec (HTB walkthroughs)
• LiveOverflow (Advanced techniques)
• John Hammond (Practical tutorials)

🏆 Certification Roadmap

Year 1:

• eJPT → OSCP → CEH (if employer requires)

Year 2:

• CRTP → CRTO → PNPT

Year 3+:

• OSEP → OSCE → CISSP (for management track)

⚠️ What NOT to Waste Time On

• Avoid: Basic IT+ certifications if you're tech-savvy
• Skip: Theory-heavy courses without practical labs
• Don't: Jump straight to OSCP without Linux/networking foundation
• Avoid: Illegal activities - always use authorized testing environments

💼 Career Progression Path

0-2 years: Junior Penetration Tester → Security Analyst 2-4 years: Penetration Tester → Red Team Operator 4-7 years: Senior Penetration Tester → Red Team Lead 7+ years: Principal Consultant → Head of Red Team Operations

🚀 Action Steps to Start Today

1. Week 1-2: Set up Kali Linux, master basic commands
2. Week 3-4: Complete TryHackMe "Complete Beginner" path
3. Month 2: Start Hack The Box, aim for 10 easy machines
4. Month 3: Begin eJPT preparation
5. Month 4: Take eJPT exam

💡 Pro Tips for Success

• Document Everything: Keep detailed notes of techniques and findings
• Build a Portfolio: Create GitHub with your scripts and writeups
• Network: Join cybersecurity communities (Discord, Reddit, Twitter)
• Stay Updated: Follow security researchers and read vulnerability reports
• Practice Daily: Consistency beats intensity

This roadmap is specifically designed to avoid time-wasting and focus on practical, job-relevant skills. The progression is logical, building each skill upon the previous ones, and directly addresses your interests in red teaming, scripting, and penetration testing.

Start with Phase 1 and don't skip the fundamentals - they're crucial for everything that follows. Good luck on your cybersecurity journey!