CTF CHALLENGE LOG

The first time I launched a Starting Point machine on Hack The Box, I had no idea what I was doing. I had the drive, I had some background from years ago, but I was staring at that terminal thinking, “Okay… now what?” Fast forward a bit, and things have changed. I’m chaining exploits, writing cleaner payloads, recognizing patterns in web apps, pulling off privilege escalation, and actually enjoying it. The wins come faster now — but so do the "aha" moments when something clicks that didn’t before. It’s wild to look back and realize how much growth has happened in a short time. Every reverse shell, every dead end, every “why the hell isn’t this working” moment taught me something. HTB has been more than just practice — it’s been a proving ground. Not to prove anything to anyone else, but to myself. That I can still learn. That I still love this. That I’ve still got it. If you’re early in the journey: don’t let frustration stop you. Keep banging your head against the wall. Eventually it breaks.

If a door is closed, use the window. If the window is locked, use the ventilation shaft. This one taught me that a seemingly benign script can be used to break a system. This was a fun challenge and definitely had me scratching my head a few times. For me, one big takeaway is that sometimes it's just as important to not only look at what a script is doing, but how it is being done.

When I first started this journey, I felt like I was on fire — working through Starting Point and easy boxes, making solid progress. I knocked out four in a weekend. The linear structure of those early challenges made it feel like I was actually getting good at this. Turns out, that was kind of a trap. Now that I’m digging into medium boxes, I’m seeing just how wrong I was. It’s not always “unlock this to get to the next thing.” Sometimes, the path forward is something I overlooked hours (or days) ago — something I dismissed as a dead end, only to realize later that I just didn’t know enough yet to recognize it for what it really was. I’m not going to lie — I gave up on this box three separate times. I was stuck in that mindset of pushing forward, head down, trying to brute-force my way through. What finally cracked it open for me was stepping back, revisiting earlier steps with fresh eyes, and realizing how much I’d learned without even noticing. That epiphany? That’s the real progress. I’m hoping the more I do this, the more of those moments I’ll have — because at the end of the day, getting good at this is about learning how to think about these systems, and how to recognize weaknesses and vulnerabilities — not just checking off boxes.

Just finished my first medium-difficulty box on Hack The Box. This one really challenged me and pushed much harder than any of the "easy" boxes I've done. It forced me to slow down, think more critically, and refine my process. It’s less about tools and more about context. Less brute force, more finesse. When something didn’t work, I didn’t see it as failure—I saw it as feedback. I didn’t beat this box—I just didn’t let it beat me. It reminds me of learning to ski. Once I had the basics, I kept running the same mogul trail until I was ready to throw my skis off the mountain. But every time I fell, I picked myself up, dusted myself off, and got back on the lift. Even when I wanted to give up and sit by the fire, I kept going until it worked.

I spent hours feeling completely stuck—knowing the initial foothold was right there. Every path felt like a dead end. Tried the usual tricks, overthought the hard parts, second-guessed everything. The breakthrough didn’t come from some elite exploit. It came from slowing down, reading between the lines, trusting the process, and pushing through the frustration.