Penetration Testing With Honest-To-Goodness Malware

When did penetration-testing methodologies stop replicating the vectors attackers make?

Gunter Ollmann, CTO, Security, Microsoft Cloud and AI Division

October 1, 2013

3 Min Read
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Popular fiction usually dictates that the primary cyberfoe of big business is a young, nerdish, and exceedingly smart computer hacker with a grudge against practically anyone and everyone. It may be this particular cliched (and false) stereotype of a hacker that many business analysts and executives have, in turn, used as justification for testing the defenses of their organizations in a particular way. While some may supplement this image of a hacker with concrete bunkers filled with uniformed cyberwarriors if they feel worthy of state-initiated attacks, it is a sad fact that many of the methodologies currently employed by organizations to evaluate their tiered defenses are tired and dated.

The reality of the situation is that organizations are much more likely to be breached through fairly average malware than through the deliberate and chained exploitation of system vulnerabilities. That's not to say "classic" hacking isn't a problem, but the scale of the threat today is like battling mosquitoes while ignoring the lion gnawing at your arm.

Modern penetration-testing methodologies continue to follow a very predictable pattern,and practically every assessment I've ever been involved in or have overseen during the past decade has yielded vulnerabilities that were critical in nature. While these vulnerabilities are flagged for remediation and are often fixed within days of identification, the organization is still left to battle a barrage of social-engineering attacks designed to install malware on victim devices and to serve as jump points into other sectors of the business.

In recent years, organizations have increased the number and sophistication of the defensive layers they use to battle malware-based intrusion. In general, these defenses have improved the security stature of those organizations that make the investment. However, the increased need for roaming user support, BYOD, encrypted communications, and third-party app markets has, in turn, exposed those same organizations to new kinds of attack vectors for which they have little appreciation of the dynamics of the threat or the ability to quantify the status of their recently deployed anti-malware defenses.

It has become necessary for penetration-testing methodologies to better reflect the true nature of the threat and to replicate the methods used by an attacker. In particular, penetration testers need to now incorporate malware and malware-specific delivery techniques into their testing routines.

As trivial as it may seem, including malware into a penetration test or security assessment is not a simple task. The variety of delivery vectors and the effort needed to stage an attack is something few penetration testers have had to involve themselves with in the past. There's also the complexity of crafting malware-based payloads that not only report back their successes, but also provide for rapid cleanup after an engagement is over.

That said, it would be remiss of security consultants or ethical hackers to not test the robustness and capability of their clients' networks to counter malware-based threat vectors. The choice to not employ malware for lateral movement and compromise within a client's network may be a reflection of inadequate scoping or a poor understanding of the modern threat spectrum.

Regardless, the onus is on security consultants to duplicate the means and capability of a modern hacker -- and, by foregoing malware, they are playing to outdated threats and past stereotypes.

-- Gunter Ollmann, CTO, IOActive Inc.

About the Author

Gunter Ollmann

CTO, Security, Microsoft Cloud and AI Division

Gunter Ollmann serves as CTO for security and helps drive the cross-pillar strategy for the cloud and AI security groups at Microsoft. He has over three decades of information security experience in an array of cyber security consulting and research roles. Before to joining Microsoft, Gunter served as chief security officer at Vectra AI, driving new research and innovation into machine learning and AI-based threat detection of insider threats. Prior to Vectra AI, he served as CTO of domain services at NCC Group, where he drove the company's generic Top Level Domain (gTLD) program. He was also CTO at security consulting firm IOActive, CTO and vice president of research at Damballa, chief security strategist at IBM, and built and led well-known and respected security research groups around the world, such as X-Force. Gunter is a widely respected authority on security issues and technologies and has researched, written and published hundreds of technical papers and bylined articles.

Originally, Gunter had wanted to be an architect but he lost interest after designing retaining walls during a three-month internship. After that, he qualified as a meteorologist, but was lured to the dark side of forecasting Internet threats and cyberattacks. His ability to see dead people stoked an interest in history and first-millennium archaeology.

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