Each year, Rapid7 penetration testers complete hundreds of internally and externally based penetration testing service engagements. This post is part of an ongoing series featuring testimonials of what goes on beneath the hoodie. For more insights, check out our 2020 Under the Hoodie report.

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During one penetration test for an energy company, I started off by scoping out the client’s facility, a high-fence compound that stored commercial construction equipment and vehicles. There was no way to walk into this facility, since vehicles were only allowed in and out using a proximity card to grant them access.

I saw there were some other businesses lining one side of the fence, but there weren’t enough people around to keep my presence undetected. When I came back to the facility at night, I was excited to find everyone at the neighboring businesses had gone home. Under the cover of these now-empty buildings, I was able to scale the fence to access the facility.

At the same time, I was slacking with other penetration testers who were working the same assessment in different locations. Our Slack channel was filled with battle music, infosec memes, and words of encouragement. This was just the extra boost I needed to continue my quest.

I proceeded to look for interesting targets while I stayed in the shadows, living out my childhood ninja fantasies. I saw a bunch of big, commercial-sized trucks parked around the facility, so I climbed up the rear passenger-side door of one of the more concealed trucks to peek inside. Bingo: Right on the arm rest was a laptop.

I tried all the doors of the truck, walking around as inconspicuously as one can in a gated area at night, trying to break into a commercial truck. Unfortunately, all of them were locked.

I then turned my attention toward the triangle-sized vent window of the passenger front door. It was closed, but to my surprise, it wasn’t locked. I pushed it open, reached inside, and unlocked the passenger door to grab the laptop.

Voila! Game save.

Interested in learning more about how Rapid7 pen testers conduct their assessments? Check back every week for a new story in the series.

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