So, I spent a good chunk of my week wrestling with a simulated DISA data breach. You know, trying to get a feel for what it’s like when things go south in that kind of environment. It’s one thing to read about it, another to actually get your hands dirty, even in a lab.
Setting the Stage
First off, I had to cobble together a testbed. Nothing too crazy, just a couple of virtual machines. One I configured to be a ‘target’ – think a generic server that’s supposed to be somewhat hardened, maybe following some STIG baselines, or at least attempting to. The other VM was my ‘attacker’ machine. The goal wasn’t to be super sophisticated on the attack side, but more to see what kind of tracks common techniques would leave and how easy, or hard, they’d be to spot.

I decided to simulate a few common entry points.
- A bit of simulated phishing – basically, ‘tricking’ a dummy user account.
- Then, once ‘inside’, I tried some basic privilege escalation. Nothing groundbreaking.
- And finally, I poked around to see if I could ‘exfiltrate’ some dummy data.
The Nitty-Gritty
Man, the moment I started, it was clear this wasn’t going to be a walk in the park. Even with a simplified setup. My primary focus was on the detection and response side from the ‘defender’s’ perspective. So, after my ‘attacker’ VM made some moves, I switched hats.
Log diving was the name of the game. I started sifting through system logs, application logs, whatever I had configured. The sheer volume, even on a couple of VMs, can be a lot. It’s like looking for a specific grain of sand on a beach. I tried to set up some basic alerts, but tuning them to catch the ‘bad’ stuff without getting a million false positives? That’s an art form in itself.
I found that just because a system is ‘compliant’ on paper doesn’t mean it’s magically going to scream when something fishy happens. Those STIGs are comprehensive, no doubt. But they are a baseline. The real work is in making sure everything is actually reporting correctly, that the dots are connected, and that someone is actually watching and understanding what they’re seeing.
What I Bumped Into
One thing that really hit home was the importance of endpoint visibility. Server logs are great, network logs too, but seeing what’s happening right there on the compromised machine? Priceless. If that’s not being captured or forwarded properly, you’re flying half-blind.
And the tools… well, some tools are better than others. Some make it easier to correlate events, others feel like you’re trying to assemble a jigsaw puzzle in the dark. I wasn’t using anything super advanced, mostly built-in stuff and some open-source utilities. It reminded me that it’s not always about having the fanciest gear, but knowing how to squeeze every bit of information out of what you’ve got.
It’s kinda like trying to manage a big, complex project where everyone has their own piece. In a real DISA environment, you’d have so many different systems, different security layers, different teams. Getting them all to talk to each other and present a clear picture during an incident? That’s a massive challenge. My little two-VM setup gave me just a tiny taste of that complexity.
This whole exercise really hammered home that readiness isn’t a one-time checklist. It’s a constant process. You set things up, you test them, you find the holes, you fix them, and then you test them again. Because the other side, they’re always poking, always adapting. It’s a bit of a grind, to be honest, but absolutely necessary.