Penetration Testing on System Overlord

Raspberry Pi as a Penetration Testing Implant (Dropbox)

david@systemoverlord.com (David Tomaschik) — Tue, 14 Jul 2020 00:00:00 +0000

Sometimes, especially in the time of COVID-19, you can’t go onsite for a penetration test. Or maybe you can only get in briefly on a physical test, and want to leave behind a dropbox (literally, a box that can be “dropped” in place and let the tester leave, no relation to the file-sharing company by the same name) that you can remotely connect to. Of course, it could also be part of the desired test itself if incident response testing is in-scope – can they find your malicious device?

In all of these cases, one great option is a small single-board computer, the best known of which is the Raspberry Pi. It’s inexpensive, compact, easy to come by, and very flexible. It may not be perfect in every case, but it gets the job done in a lot of cases.

I’ll use this opportunity to discuss the setups I’ve done in the past and the things I would change when doing it again or alternatives I considered. I hope some will find this useful. Some familiarity with the Linux command line is assumed.

So You Want to Red Team?

david@systemoverlord.com (David Tomaschik) — Tue, 26 Mar 2019 00:00:00 +0000

So there’s a lot of confusion out there about Penetration Testing and Red Teaming. I wanted to put together a list of resources for those familiar with infosec or penetration testing who want to get into red teaming or at least get a better understanding of the methodologies and techniques used by red teamers.

First, it’s important to note that Red Teaming is predominantly comprised of two things: alternative analysis and adversary simulation. Red teams do not attempt to find “all the vulnerabilities” and do not usually try to have a wide breadth of coverage. Instead, red teams seek to simulate an adversary with a particular objective, predominantly to act as a “sparring partner” for blue teams. Keep in mind, red teams are the only adversary that will debrief with the blue team so that blue team can figure out what they missed or could have done differently.

For more about the specific definition of Red Teaming, check out the presentation Red Teaming Probably Isn’t For You by fellow red teamer Toby Kohlenberg.

Getting Started in Offensive Security

david@systemoverlord.com (David Tomaschik) — Mon, 18 Sep 2017 00:00:00 +0000

Please note that this post, like all of those on my blog, represents only my views, and not those of my employer. Nothing in here implies official hiring policy or requirements.

I’m not going to pretend that this article is unique or has magic bullets to get you into the offensive security space. I also won’t pretend to speak for others in that space or in other areas of information security. It’s a big field, and it turns out that a lot of us have opinions about it. Mubix maintains a list of posts like this so you can see everyone’s opinions. I highly recommend the post “So You Want to Work in Security” by Parisa Tabriz for a view that’s not specific to offensive security. (Though there’s a lot of cross-over.)