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So... You Want to Become a Penetration Tester?

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Cybersecurity is a rapidly growing and evolving field with a wide range of subfields and specializations. One of these is penetration testing, a discipline within what's known as "red teaming," which seeks to actively find and exploit vulnerabilities within computer systems (with permission, of course).

It's an exciting and rewarding career, and I'll show you how to become a penetration tester.

Before I continue, however, let me be transparent about my own experience. While I have about three years of ethical hacking experience, I have just over a year of professional penetration testing experience. During that time, I earned the GIAC Certified Penetration Tester (GPEN) certification. In addition, I have 15 years of experience in the IT field, most of it in networking and network security (firewalls, IDS/IPS, etc.), with a stint as a digital forensics analyst.

I also hold a Master's degree in computer science with a focus on information assurance. My thesis centered on undergraduate cybersecurity education, where I taught students how to hack Wi-Fi and defend against such attacks. I share this not only to be honest about my hacking experience but also to establish my cybersecurity "bona fides" so to speak.

As stated earlier, penetration testing involves finding and exploiting various vulnerabilities, then reporting those findings to the system owner. Penetration testing differs from other forms of ethical hacking in that it requires the explicit permission of the system owner. That permission typically includes a detailed scope (what you're allowed to test) and rules of engagement (what you're allowed to do).

That brings us to the knowledge and skills required to conduct a thorough penetration test.

The Basics

Unless you already have a technical background, acquiring these skills will not be easy. Cybersecurity is NOT an entry-level field. To hack computers, you must first understand how they work. Here's a quick and dirty roadmap if you're completely new to tech:

1. Learn how computers work

This will give you a basic understanding of computer hardware and operations. It generally covers topics such as the parts of a computer (CPU, RAM, GPU, etc.), installing and configuring operating systems, basic scripting, and troubleshooting.

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