Beginner's Guide to Penetration Testing

🚀 Introduction

Becoming an offensive security professional is not about shortcuts — it’s about building a strong foundation and mastering the basics. Like many others, I started by exploring everything without a clear direction. Eventually, I realized that having a structured roadmap makes all the difference.

Coming from a Networking & Windows Server administration background, web security was my weak point. Over time, I achieved certifications such as eJPTv2, PNPT, CRTA, CRTP, and CRTO, alongside practical learning through TryHackMe (Junior Penetration Tester, Offensive Security, Web Fundamentals, AD attack & enumeration) and countless labs.

👉 Good hackers don’t guess — they understand how things really work. good foundation is everything, the good hacker don't guess but understand how things really work.

This article outlines the roadmap I used to build my offensive security skillset.

🧩 Step 1 – Build a Strong Foundation

🌐 Networking

Network Fundamentals
Wireshark
Network Security
Network Exploitation Basics

🕸️ Web Basics

How the Web Works
Web Hacking Fundamentals
Burp Suite Essentials

💻 Operating Systems

Linux Fundamentals
Windows & Active Directory Fundamentals
Cryptography

⌨️ Power of the Terminal

Command Line Mastery

🐍 Scripting

Scripting for Pentesters

🔐 Step 2 – Cybersecurity Fundamentals

Introduction to Cyber Security
Security Engineering Basics
Introduction to Offensive & Defensive Security
Vulnerability Research
Security Solutions
Introduction to Pentesting

🛠️ Step 3 – Hands-On Hacking Practice

Understanding tools is one thing; knowing how they work under the hood is another.

Pentesting Tools
Offensive Security Tooling
Exploitation Basics
Privilege Escalation
Shell & Access Management
Common Attacks
Breaching Active Directory

Once you’re comfortable with the first three steps, your real offensive security journey begins.

✅ To-Do List

Complete all the easy rooms on TryHackMe
Follow the Offensive Pentesting, Junir Penetration tester, Web fundamentals, Networking path

🎯 What’s Next?

Once your foundation is solid, it’s time to specialize:

Web Application Pentesting (via TryHackMe & PortSwigger Academy)
Red Teaming (simulate advanced attackers)
HackTheBox CBBH certification prep

As you progress, challenge yourself with medium and hard labs. If you get stuck, it’s okay to check a write-up or walkthrough — but always come back and try again on your own.

📝 The Importance of Note-Taking

A crucial habit in your journey is note-taking. Every test, every lab, every attack path should be documented. This not only reinforces your learning but also prepares you for real-world engagements.

A good structure for write-ups includes:

Information Gathering
Scanning & Enumeration
Vulnerability Research
Exploitation
Privilege Escalation
Post-Exploitation
Lateral Movement
Pivoting
Reporting

📚 Resources

Here are some useful resources to kickstart your journey using Tryhackme:

🔗 TryHackMe — Practical labs for hands-on learning
🧪 PortSwigger Academy — Free web application security training
⚡ HackTheBox — Advanced labs and certifications

🏁 Final Thoughts

Offensive security is not just about tools or exploits — it’s about understanding systems deeply, thinking like an attacker, and documenting everything you learn.

This roadmap is not a race. Take your time, practice daily, and never stop learning.

“The journey of an offensive security professional isn’t about becoming a script-kiddie hacker. It’s about building mastery, one layer at a time.”

Stay consistent, keep hacking, and see you at the top. 🚀

🛡️ Roadmap to Becoming an Offensive Security Professional

Comments (1)

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🚀 Introduction

🧩 Step 1 – Build a Strong Foundation

🌐 Networking

🕸️ Web Basics

💻 Operating Systems

⌨️ Power of the Terminal

🐍 Scripting

🔐 Step 2 – Cybersecurity Fundamentals

🛠️ Step 3 – Hands-On Hacking Practice

✅ To-Do List

🎯 What’s Next?

📝 The Importance of Note-Taking

📚 Resources

🏁 Final Thoughts

Command Palette

Comments (1)

Pentesting

How to install Metasploitable2 on docker — step-by-step

More from this blog

🚀 Introduction

🧩 Step 1 – Build a Strong Foundation

🌐 Networking

🕸️ Web Basics

💻 Operating Systems

⌨️ Power of the Terminal

🐍 Scripting

🔐 Step 2 – Cybersecurity Fundamentals

🛠️ Step 3 – Hands-On Hacking Practice

✅ To-Do List

🎯 What’s Next?

📝 The Importance of Note-Taking

📚 Resources

🏁 Final Thoughts