Callaway’s Cyber Digest

The PTES pentesting standard is awesome and you should read it

If you’re into pentesting or red teaming, sooner or later you’ll encounter some standardized methodologies.

The National Institute of Standards and Technologies (NIST) has one called the “Technical Guide to Information Security Testing and Assessment,” or SP800-115. I’m a big fan of NIST, and this is a good place to start, especially if you care about FISMA risk management frameworks. But it’s pretty high-level, and will probably leave you wanting more.

With a little more Googling, you’ll then find pentest-standard.org. The page has a dated MediaWiki interface. It hasn’t been updated in almost a year. But those things don’t matter, this site is made of open source awesomeness.

The meat of the site lives in the PTES Technical Guidelines. It’s fairly extensive, and if you’re already somewhat familiar with information security, it can go a long way to teaching you about penetration testing.

To give you an idea of the scope of this methodology, take a look at the FreeMind map that they posted, converted here to PNG for your viewing ease.

penetration_testing_execution_standard

Go ahead and click on it, you’ll need to load the whole thing then zoom. It’s enormous.

Every one of these entries in the mindmap are backed up by some direction in the Technical Guidelines. Granted, PTES doesn’t hold your hand in all places, but for the devoted student of pentesting, this is invaluable stuff.

Now, to be fair, PTES is not the only game in town. There are other methodologies worth mentioning; I’ll write more about the later, but here’s an overview.

OWASP is another open source pentesting framework, but it’s focused at the web application layer. 18F, the folks behind cloud.gov and other cool stuff, requires the use of an OWASP automated scanner called ZAP as part of the ATO process.

ISSAF is another cool methodology, but it’s even harder to navigate than PTES. You can download the rar archive, or navigate the individual .doc files. At some point I hope to map PTES and ISSAF steps to one another to identify gaps in the former and contribute back to the project.

As much as I like it, PTES could really use a little TLC. There are incomplete sections. And a more modern interface would help, possibly even a migration to a GitHub Pages model, which would make community contribution easier. A D3 directed graph (example) would make for a nice, interactive mindmap.

But despite its shortcomings, I’d say it’s still the best open source pentesting methodology out there. Go check it out.

Callaway’s Cyber Digest

Callaway’s Cyber Digest

Callaway’s Cyber Digest

Origins of the term “cyber”

I used to rail against the term “cyber.” As one who grew up during the transitional period between ARPANET and the Internet, “cyber” took on ridiculous meaning. One learned quickly to avoid anyone whose avatar — or blinking cursor back then — asked, “wanna cyber?” Visions of Max Headroom doing unspeakable things were, for me, mentally far too near.

Earlier this year, Fred Kaplan published an excellent book called Dark Territory: The Secret History of Cyber War. It was this book that completely changed my mind.

I’m now happy to admit that the term, “cyber,” is actually really cool.

First, let’s look at the origin of the word. Wikipedia tells us that the cyber prefix comes from the word, “cybernetic.” This is cool in and of itself, because the word “cybernetics” dates all the way back to Plato. Digging deeper, we see that the etymology of cybernetics comes from a word familiar to the DevOps world: κυβερνήτης, or transliterated, kubernetesEtymonline confirms it:

cybernetics (n.)
coined 1948 by U.S. mathematician Norbert Wiener (1894-1964) from Greek kybernetes “steersman” (metaphorically “guide, governor”)

This is already pretty great, but the rabbit hole goes deeper. Back to Kaplan (pp. 44-45):

What to call these “other” threats? One word was floating around in stories about hackings of one sort or another: “cyber.” …the term stemmed from William Gibson’s 1984 science-fiction novel, Neuromancer, a wild and eerily prescient tale of murder and mayhem in the virtual world of “cyberspace.”

Kaplan goes on to describe how a Justice Department attorney named Michael Vatis had just read Neuromancer, and suggested they use the term during the development of the Marsh Report. This pleases me greatly, as Neuromancer is probably one of my top three favorite books of all time.

So there you have it — Plato, William Gibson, and Kubernetes all tied up in one awesome word. Now when you hear terms like cyberwar, cybercrime, cyber-anything you can rest assured that the term is not lame, but indeed, quite kick-ass.