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🚀 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 Section	Key Concepts & How to Learn	Icon
1. Core Networking Knowledge	Concepts: 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 Knowledge	Linux (Primary OS): Install a Virtual Machine (e.g., VirtualBox ) with Kali Linux . Learn commands: ls, cd, grep, find, chmod, ps, and service management.
Windows: Understand basic command line (cmd and PowerShell), file system, and user management.
3. Introduction to Cybersecurity Concepts	Concepts: 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 Section	Key Concepts & Tools	Icon
1. The Hacking Methodology	Follow a structured approach like the PTES : Pre-engagement, Intelligence Gathering, Threat Modeling, Vulnerability Analysis, Exploitation, Post-Exploitation, and Reporting.
2. Essential Tools & Techniques	Reconnaissance: whois, nslookup, dig, theHarvester, Maltego .
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 Phase	Platforms: 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 Section	Key Focus Areas	Icon
1. Intense Practice	Continue challenging yourself on TryHackMe and Hack The Box. Explore PortSwigger’s Web Security Academy  for web app practice.
2. The Art of Reporting	Structure: 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 Specialization	Deepen 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 Section	Key Preparation Steps	Icon
1. Get a Certification	Highly 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 Interview	Technical: 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.

🎯 Penetration Testing Learning Roadmap

 

 Penetration Testing Learning Roadmap

This roadmap is divided into three phases, emphasizing hands-on practice in each stage.

Phase 1:  Foundational IT & Security (3-6 Months)

You need a solid IT and networking background, as all hacking relies on understanding how systems work.

Content Section	Key Topics to Learn	Icon
Networking Fundamentals	TCP/IP (the language of the internet), OSI Model, Ports and Protocols (e.g., HTTP, DNS, DHCP), Subnetting, basic router/switch concepts.
Linux Mastery	Command Line Interface (CLI) essentials, file system navigation, permissions, Bash Scripting (for basic automation), package management. Kali Linux is the industry standard for pen testing tools.
Operating Systems	Fundamentals of Windows (user accounts, permissions, registry, services) and Linux. Understanding system architectures.
Programming/Scripting	Python is the most crucial language for a pen tester (used for scripting, automating tasks, and writing custom tools). Learn the basics of data types, loops, functions, and file handling.
Basic Security Concepts	CIA Triad (Confidentiality, Integrity, Availability), Cryptography basics, Hashing, Firewalls.
Virtualization	Setting up a virtual lab using tools like VMware or VirtualBox to practice legally and safely.

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Phase 2:  Core Penetration Testing Skills (6-12 Months)

This is where you learn the methodologies and tools to conduct an actual penetration test.

Content Section	Key Topics to Learn	Icon
Methodology & Scoping	Penetration Testing Lifecycle (Planning, Recon, Scanning, Exploitation, Post-Exploitation, Reporting). Understanding Rules of Engagement.
Information Gathering (Recon)	Passive Recon (Google Dorking, WHOIS, OSINT), Active Recon (Ping Sweeps, Port Scanning).
Scanning & Enumeration	Mastering Nmap (port scanning, service detection, Nmap Scripting Engine), Vulnerability Scanners (e.g., Nessus, OpenVAS basics).
Web Application Pen Testing	The OWASP Top 10 (SQL Injection, XSS, Broken Authentication, etc.), and learning to use Burp Suite (the primary web proxy tool).
Network Pen Testing	Exploiting common services, simple Metasploit framework usage, password cracking (e.g., Hashcat/John the Ripper basics), Man-in-the-Middle (MITM) attacks.
Exploitation & Post-Exploitation	Understanding different types of exploits, gaining a shell, and basic Privilege Escalation (going from a low-level user to an administrator/root).
Reporting	The most critical soft skill: Documenting your findings clearly, creating proof-of-concept, and suggesting remediation steps.

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Phase 3:  Advanced Topics & Specialization (Ongoing)

Once you’re comfortable with the core skills, you can delve into more complex, real-world attack scenarios relevant to a company environment.

Content Section	Key Topics to Learn	Icon
Active Directory Attacks	Understanding and exploiting the most common corporate environment: Windows Active Directory. Techniques like enumeration, domain lateral movement, and Kerberos attacks.
Advanced Web Exploits	Deep dives into Server-Side Request Forgery (SSRF), Business Logic Flaws, and API penetration testing.
Cloud Security Basics	Introduction to common security misconfigurations in AWS/Azure (especially important for modern companies).
Scripting for Custom Tools	Writing more complex Python scripts for automation, parsing data, and customizing payloads.
Certifications Prep	Studying for a well-respected entry-level certification like CompTIA PenTest+ or the highly regarded, hands-on Offensive Security Certified Professional (OSCP) (consider this after a few months of Phase 2).
Real-World Practice	Solving complex boxes/labs on platforms like Hack The Box and TryHackMe.

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 Learning Resources & Practical Advice

The best way to learn pen testing is by doing. Hands-on experience is what your customer will interview you on.

1. Guided Learning Platforms:
   • TryHackMe: Excellent for absolute beginners. Their “Pre-Security” and “Complete Beginner” learning paths cover Phase 1 and most of Phase 2 in a gamified way.
   • Hack The Box Academy: Offers structured learning modules with hands-on labs that are great for building practical skills.
2. Free Courses:
   • The Cyber Mentor’s (TCM Security) Practical Ethical Hacking course (often available for free or cheap on platforms like Udemy) is widely recommended for its practical approach.
   • Look for free introductory courses on platforms like Coursera or edX from institutions like IBM or EC-Council.
3. Community & Documentation:
   • Join cybersecurity communities on platforms like Discord or Reddit (e.g., r/netsec, r/HowToHack).
   • Read the documentation for essential tools like Nmap, Burp Suite, and Metasploit.

Crucial Interview Preparation Tip:

• Document Everything: As you practice, meticulously document every step, command, and finding in a professional manner. Your final output as a pen tester is a report. Your customer will likely test your ability to explain your process and findings clearly—this demonstrates your professional value.
• Focus on the “Why”: Don’t just learn how to run a tool; understand why the vulnerability exists and how to fix it (remediation). This shows a holistic security mindset.