Navigating Complex Systems: A Small Conversation with a Skilled Penetration Tester

I recently had a chance to catch up over coffee with my colleague who is quite skilled in penetration testing. As we chatted about our current projects and industry trends, I took the opportunity to ask them about their unique approach to tackling complex systems and finding vulnerabilities. Grab your beverage of choice and join us!

The chat

Working together on pentests, I've noticed that you're fantastic at filtering out noise and zoning in on crucial aspects. You manage to ask incredibly precise questions that hit the mark even when navigating multiple system layers. Is this just down to experience, or is there something more going on – perhaps a unique talent or specific methodology?

For me, it's all about my methodology.

I've come across people who seem like they have superpowers when it comes to targets, spotting vulnerabilities in an instant. But those same individuals often struggle with consistency and covering all their bases.

My approach is pretty straightforward:

1. Visualize the entire system as one big picture ("the cake").
2. Divide it into manageable chunks that you can work through systematically.
3. Whenever you stumble upon something that could affect other parts of the system, note where you are and investigate potential repercussions.

When I hit a wall or can't figure something out – which happens more often than not – I try to think about potential ways to gain some clarity. Maybe it involves looking up code references or running dynamic tests. The goal isn't necessarily to identify vulnerabilities right off the bat, but rather to deepen my understanding of the target.

How do you usually divide "the cake"? By components or specific areas?

I break it down into bite-sized chunks. If a chunk is too large for me to grasp all at once, I've likely cut it too big. This isn't something I do just once; I continually reassess and adjust throughout the pentest.

How do you know when to stop digging? You could easily fall down the rabbit hole with each piece.

When you find yourself really lost or unsure about what you're hunting for, that's when you should pause and reassess. It's okay to get a bit lost here and there, but taking a moment to refocus on your objectives can help you get back on track. Notes are invaluable here – jotting down progress, coverage, and questions (no matter how trivial) keeps me on point.

Do you keep paper notes?

Not typically. Paper is great for schematics, but I prefer not lugging any around with me if I can help it.

But isn't all that note-taking time-consuming?

Not really. You're not writing a blog post per endpoint; instead, you're explaining things to yourself in a couple of sentences for your own understanding. A few well-crafted sentences are usually enough for me to remember findings and determine next steps.

Outro

That's how we rolled through our coffee chat, learning from each other's experiences and methodologies. As I wrap up this post, I'm curious to hear from you, have you ever felt lost during a pentest? How did you refocus? Until then, happy hunting!