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Tuesday, 30 September 2025

🚀 Penetration Testing Roadmap

 

Phase 1: 👶 The Foundation (Months 1-2) – “Learn to Walk”

This phase is about understanding the landscape and the core concepts. You cannot attack what you don’t understand.

Content SectionKey Concepts & How to LearnIcon
1. Core Networking KnowledgeConcepts: TCP/IP model 🌐, OSI Model, IP addresses, subnets, DNS, HTTP/HTTPS, routers, switches, firewalls.📡
How to Learn: Course: Watch Professor Messer’s CompTIA Network+ video series (YouTube). Book: “Network+ All-in-One Guide” by Mike Meyers.📚
2. Basic Computer & OS KnowledgeLinux (Primary OS): Install a Virtual Machine (e.g., VirtualBox 🧪) with Kali Linux 🐧. Learn commands: lscdgrepfindchmodps, and service management.💻
Windows: Understand basic command line (cmd and PowerShell), file system, and user management.🖥️
3. Introduction to Cybersecurity ConceptsConcepts: Confidentiality, Integrity, and Availability (CIA Triad 🛡️). Vulnerabilities, threats, and risks. Authentication vs. Authorization.🧠
How to Learn: Free introductory courses on Coursera (e.g., Google’s Cybersecurity Certificate) or Cybrary.it.🎓

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Phase 2: 🏃 Core Penetration Testing Skills (Months 3-6) – “Learn to Run”

This is the hands-on phase where you start using the tools and methodologies.

Content SectionKey Concepts & ToolsIcon
1. The Hacking MethodologyFollow a structured approach like the PTES 📜: Pre-engagement, Intelligence Gathering, Threat Modeling, Vulnerability Analysis, Exploitation, Post-Exploitation, and Reporting.📝
2. Essential Tools & TechniquesReconnaissance: whoisnslookupdigtheHarvesterMaltego 🔎.🛰️
Scanning & Enumeration: Master Nmap 🗺️ (all scan types). Get familiar with Vulnerability Scanners like Nessus or OpenVAS.🚨
Exploitation: Learn the Metasploit Framework 🔥 (searching, using, configuring exploits/payloads).💣
Post-Exploitation: Privilege escalation, pivoting, and maintaining access.🔑
Web Application Hacking: Focus on the OWASP Top 10 (SQLi, XSS, CSRF, etc.) 🕸️. Tools: Burp Suite ⚙️ (industry standard) and OWASP ZAP.🕷️
How to Learn This PhasePlatforms: TryHackMe 🕹️ (start with “Jr. Penetration Tester” path). Hack The Box (start with “Starting Point”). Course: TCM Security’s “Practical Ethical Hacking” 🧑‍🏫.✅

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Phase 3: 🏅 Practice & Specialization (Months 6-9) – “Become an Athlete”

Now you need to solidify your skills and start looking like a professional.

Content SectionKey Focus AreasIcon
1. Intense PracticeContinue challenging yourself on TryHackMe and Hack The Box. Explore PortSwigger’s Web Security Academy 🌐 for web app practice.💪
2. The Art of ReportingStructure: Executive Summary, Technical Details, Risk Rating (CVSS), Proof of Concept, Remediation Steps. Your marketing background is an asset!📊
Practice: Write a simple report for every machine you compromise.✍️
3. Choose an Initial SpecializationDeepen your knowledge in one area: Web Application Pentesting (OWASP Top 10 mastery) or Network Pentesting (Active Directory 🏢 exploitation).⭐

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Phase 4: 💼 Preparation for the Interview & Job (Month 9+)

Content SectionKey Preparation StepsIcon
1. Get a CertificationHighly Recommended Starter Certs: CompTIA PenTest+ or the practical eLearnSecurity Junior Penetration Tester (eJPT). This provides concrete evidence of your skills.🥇
2. Build a “Home Lab”Set up a virtual network with vulnerable machines (e.g., from VulnHub) and document your process in a GitHub repository or blog 📝. This is your portfolio!🏠
3. Prepare for the InterviewTechnical: Be ready to explain the OWASP Top 10 and walk through a full methodology. Scenario-Based: Practice your professional response to finding a critical bug. Your Story: Be ready to confidently explain your transition, initiative, and passion for the field.