My first CTF experience

A Capture The Flag (CTF) event is a competition between security teams where they attempt to solve various security challenges to earn points. These events can be either online or in-person. In my case, the invite came from Hack-The-Box, and I was going to solo it online.

The Setup

There were a number of rules I had to adhere to. Before the start I needed to create an OpenVPN connection to a virtual machine and get ready. Once the event started, I was be given a list of challenges to choose from. Each challenge had a different point value. For each challenge I solved, I earned the corresponding number of points.

The team with the most points at the end of the event will be declared the winner. However, even though I had little hope of winning, participating I thought participating was a great way to sharpen my security skills.

Getting Started

The first few challenges were very easy  mostly exercising my linux and networking skills. Then it started to get a little more challenging.

Using linux at home really worked well for me. With multiple screens, over multiple boxes, I was able to lookup information and download apps needed to crack each puzzle. My natural approach to each puzzle helped too. The ability to think outside the box while applying a lifetime of experience had me chugging through the next dozen or so challenges pretty easily.

"I mean, who would have known that steganography would have feature after decoding a base-64 intercepted e-mail attachment posted in an obscure Reddit u/ account? Well I could link these loose pieces of information together."

The Perfect Environment

§Á¹Ãį½± was out playing in a bridge tournament and ¦Á¯½Ä± was staying with her grandmother, so I had the house to myself, and no interruptions except getting fresh beers from the fridge and walking the dog.

Advanced Challenges

Reverse shell into a box? Set it up through a poorly configured cron daemon, nc (NetCat) and a few other tricks I'd learned over the years. The challenges progressively got more complex, but each one built on fundamental security concepts and problem-solving skills.

Lessons Learned

This first CTF experience reinforced several important insights about cybersecurity:

• Breadth of Knowledge Matters: Success required drawing from years of diverse technical experience
• Multiple Perspectives: Having multiple screens and systems provided tactical advantages
• Pattern Recognition: The ability to see connections between disparate pieces of information
• Persistence Pays: Some challenges required working through multiple layers of obfuscation
• Home Lab Value: Having a well-equipped home environment was crucial for success

The CTF Mindset

What made this experience particularly rewarding was the realization that cybersecurity isn't just about technical knowledgeit's about developing a mindset that questions assumptions, follows unconventional paths, and pieces together information from multiple sources.

The challenges ranged from straightforward technical puzzles to complex multi-stage investigations that spanned different platforms and required diverse skill sets. Each successful solve reinforced the value of curiosity, persistence, and creative thinking.

While I may not have won the competition, the experience provided invaluable practice in real-world security scenarios and confirmed that years of hands-on technical experience translate well to competitive cybersecurity challenges.

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