🎯 Introducing Our Hack The Box Starting Point Series: Learning Penetration Testing Through Practice

If you're reading this, you're probably trying to learn penetration testing. Maybe you're a beginner who's heard about "hacking" and wants to understand what it really means. Maybe you're switching careers into cybersecurity. Or maybe you're already in IT and want to level up your offensive security skills.

Here's the thing: you can't learn penetration testing by reading alone. You need to get your hands dirty. You need to enumerate services, exploit vulnerabilities, and think like an attacker—all in a safe, legal environment.

That's why I'm launching a new series of walkthroughs covering Hack The Box Starting Point machines—starting with Tier 0, the free boxes designed for absolute beginners.

🔍 What Is Hack The Box?

Hack The Box (HTB) is an online platform that provides vulnerable machines for penetration testing practice. Unlike traditional tutorials, HTB gives you real systems to attack—Linux and Windows machines running actual services with real vulnerabilities.

Starting Point is HTB's beginner-friendly series. It's designed for people who are new to penetration testing and want to learn the fundamentals:

Tier 0 — Four free machines covering basic enumeration, legacy protocols, and simple exploitation
Tier 1+ — More advanced machines (requires VIP subscription)

These machines are intentionally vulnerable, legally safe to attack, and perfect for learning.

🎓 Why I'm Writing These Walkthroughs

Let me be honest: when I started learning penetration testing, I struggled. I'd read about concepts like "port scanning" or "privilege escalation" but had no idea how to actually do them in practice. I needed examples. I needed someone to show me the thinking process, not just the commands.

That's what these walkthroughs will do.

Each post will:

Walk you through the machine step-by-step — Not just the answer, but the reasoning
Explain the tools and techniques — Why we use nmap instead of just guessing, how to interpret scan results, what to do with the information
Teach the underlying concepts — What you're actually learning and why it matters in real penetration tests
Provide context — How these vulnerabilities appear in real-world systems and why they're dangerous

Important: These walkthroughs are educational. I'll show you the methodology and techniques, but you'll still need to solve the machines yourself. The walkthroughs guide you through the process, not just the answer.

📚 What to Expect

Starting with Tier 0

We're kicking off with Hack The Box Starting Point Tier 0, which includes four free machines:

Meow — Basic enumeration and legacy protocol risks (telnet)
Fawn — FTP basics and anonymous access
Dancing — SMB enumeration and network shares
Redeemer — Redis database exposure

Each machine teaches fundamental penetration testing concepts:

Reconnaissance — How to gather information about a target
Port scanning — Identifying open services and versions
Service enumeration — Understanding what services do and how to interact with them
Exploitation — Taking advantage of misconfigurations and vulnerabilities
Post-exploitation — Finding flags and understanding the system

Tier 0 is perfect for beginners because it assumes zero prior knowledge. If you've never done penetration testing before, these machines will teach you the basics step-by-step.

What Makes These Machines Different

Unlike CTF challenges that require obscure knowledge or guessing, HTB Starting Point machines focus on real-world scenarios:

Legacy protocols still in use (telnet, FTP)
Misconfigured services (anonymous access, default credentials)
Common security mistakes (exposed databases, unsecured network shares)

These are vulnerabilities you'll actually encounter in real penetration tests.

🛠 How to Use These Walkthroughs

For Beginners

Read the walkthrough to understand the concepts and methodology
Try the machine yourself before looking at solutions
Use the walkthrough as a guide when you're stuck
Experiment — try different tools, break things, learn

For Intermediate Learners

Skip ahead if a machine seems too basic
Focus on the methodology — how I approach each problem
Challenge yourself — can you solve it differently?
Apply the techniques to other HTB machines or labs

For Everyone

Don't just copy commands — understand what they do
Google is your friend — look up tool documentation, vulnerability details, examples
Take notes — write down what works and what doesn't
Join the community — HTB has forums and Discord channels

⚠️ A Few Ground Rules

Educational Purpose Only

These walkthroughs are for learning. Don't use these techniques against systems you don't own or don't have permission to test.

Legal and Ethical

Everything you learn here should be applied ethically:

Only test systems you own or have written permission to test
Follow responsible disclosure practices
Respect privacy and data
Use your skills to help, not harm

Respect the Platform

Hack The Box provides these machines for free (Tier 0) or through subscription. Follow their rules:

Don't share flags publicly
Don't abuse the infrastructure
Don't use automated exploitation tools (unless the machine specifically allows it)
Clean up after yourself

🚀 What Makes These Walkthroughs Different

You can find HTB walkthroughs all over the internet. Here's what makes mine different:

Real-World Context

I don't just show you how to solve a machine—I explain why these vulnerabilities matter in real penetration testing. How does finding an exposed telnet service relate to actual security assessments? What does anonymous FTP access teach you about securing file transfer services?

Beginner-Friendly

I assume you're starting from zero. I'll explain every tool, every command, and every step. No jargon without explanation.

Practical Methodology

I'll show you how I think about each problem. What do I check first? How do I narrow down possibilities? What do I do when I'm stuck?

Honest Learning

I'll call out when something is tricky. I'll explain mistakes I made. I'll show you that learning penetration testing is a process, not a destination.

📅 What's Coming Next

Here's the plan:

This introduction (you're reading it)
Meow — Basic enumeration, telnet, and weak credentials
Fawn — FTP enumeration and anonymous access
Dancing — SMB enumeration and network share access
Redeemer — Redis database exposure and exploitation

I'll publish walkthroughs regularly. Each post will include:

Objective — What the machine teaches
Reconnaissance — How to gather information
Enumeration — What services are running and how to interact with them
Exploitation — How to gain access
Post-exploitation — Finding the flag
Key Takeaways — What you learned and why it matters

💡 Why This Matters

Penetration testing is a practical field. You can't learn it from books alone. You need to:

Enumerate real services
Exploit real vulnerabilities
Think creatively
Learn from mistakes

Hack The Box Starting Point provides a safe, legal environment to do exactly that. And these walkthroughs will help you get the most out of them.

Whether you're a complete beginner or someone looking to sharpen your skills, I hope these walkthroughs help you on your penetration testing journey.

🎯 Ready to Start?

The first walkthrough—Hack The Box Starting Point: Meow—will be published next. This machine teaches:

Basic enumeration — Using ping to verify connectivity
Port scanning — Using nmap to discover open services
Legacy protocols — Understanding the risks of telnet
Weak credentials — The dangers of default passwords

Meow is perfect for complete beginners—if you've never done penetration testing before, this machine will get you started with the fundamentals.

Questions about Hack The Box or this series? Reach out directly:

Email: m1k3@msquarellc.net
Phone: (559) 670-3159
Schedule: Book a free consultation

M Square LLC
Cybersecurity | Penetration Testing | No-Nonsense Advice

Introducing Our Hack The Box Starting Point Series: Learning Penetration Testing Through Practice