This content originally appeared on Level Up Coding - Medium and was authored by AJ
Overconfident, Underprepared, and Utterly Humbled
I walked into my first professional penetration test armed with textbooks, a head full of theory, and the unshakable confidence of someone who had rooted countless virtual machines in a controlled lab. I walked out eight hours later, humbled, exhausted, and with a completely rewritten understanding of what real security looked like. The client was a small financial services firm. Their fear was palpable. My job was to be their worst nightmare, and I was terrified I’d be a disappointment.
The scope was simple: gain access to their internal network and see how far I could go. I started with the flair I thought a hacker should have, launching sophisticated network attacks and trying to exploit complex service vulnerabilities. Hours ticked by. Nothing worked. Their defenses were modern and robust. My confidence, once so high, began to curdle into panic. The client was paying for results, and I had none.
The Glaring Mistake: Ignoring the Human Layer
Privilege and a Pack of Cookies
Frustrated and out of ideas, I took a break. I sat in my car, ate a pack of cookies, and decided to go back to the absolute basics: Open-Source Intelligence (OSINT). I combed through social media, old press releases, and employee review sites. On a LinkedIn post celebrating a work anniversary, I hit paydirt.
A system administrator had posted a photo of his team. In the background, on a whiteboard, was a network diagram. It was slightly blurred, but readable. More importantly, tucked in the corner of his desk was a box of a specific brand of cookies. The same kind I was eating. It was a ridiculous, human detail. I had a potential username from his email address, and now a possible password based on a brand he liked.
I returned to my keyboard, my earlier complex attacks abandoned. I tried a simple password spray attack: the brand name of those cookies with a common numerical suffix. On the third variation, the VPN portal accepted it. I was in. Not with a brilliant exploit, but with a snack food and a social media post. I had wasted half a day trying to be a movie hacker when the simplest vector was right in front of me.
The Win: Chaining Access into Catastrophe
From a Foot in the Door to the Keys to the Kingdom
My initial access was low-level. But that first credential was a foothold. Once inside the network, I could move laterally. I used the access to enumerate the Active Directory environment. I found a shared drive containing, unbelievably, a spreadsheet named “IT_Service_Accounts.xlsx.” It was not encrypted. It was not even password-protected.
The spreadsheet contained a list of service account credentials, including one for a domain administrator. The password was a variation of the company’s name and founding year. I used it. In moments, I had complete and total control over their entire digital infrastructure: every server, every workstation, every file share. The sheer scale of access was terrifying. I could have deleted everything.
The Hardest Lesson: The Report is the Job
The Hack is Fun. The Impact is Work.
The exhilaration of “owning” the network lasted about five minutes. Then the real weight of the job settled on me. This wasn’t a game. This was a company’s livelihood. My next task was the most important and the most difficult: writing the report.
I couldn’t just say “I pwned you.” I had to explain the exact series of failures in a way that a non-technical manager could understand. I had to prioritize the risks: the exposed service account was a critical finding; the weak password was a high-risk finding. I had to provide clear, actionable remediation steps for each one. The technical exploit was only 10% of the job. The other 90% was communication and context.
The Lesson That Stuck
That first pentest taught me that security isn’t about fancy zero-days or complex code execution. It’s about the fundamentals. It’s about passwords on sticky notes, unsecured files on shares, and the oversharing of information online. The most devastating attacks are often the simplest.
It also taught me humility. The goal isn’t to look like a genius; it’s to make the client safer. Sometimes that means admitting your first approach was wrong and starting over. That day, I didn’t just learn how to be a better hacker. I learned how to think like one. And it all started with a pack of cookies and a moment of quiet desperation.
The gap between theory and practice is where real security is learned. If you want more stories from the front lines and actionable lessons from real-world breaches, give me a follow. The journey is just beginning.
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Inside My First Real-World Pentest: Mistakes, Wins, and Lessons was originally published in Level Up Coding on Medium, where people are continuing the conversation by highlighting and responding to this story.
This content originally appeared on Level Up Coding - Medium and was authored by AJ
AJ | Sciencx (2025-08-28T20:42:50+00:00) Inside My First Real-World Pentest: Mistakes, Wins, and Lessons. Retrieved from https://www.scien.cx/2025/08/28/inside-my-first-real-world-pentest-mistakes-wins-and-lessons/
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