Research / Article

Untested Is Untrusted: Penetration Tests and Red Teaming Key to Mature Security Strategy

Understand how penetration tests and red team exercises can strengthen your organization’s security posture against threats.

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Organizations need to know how well their defenses can withstand a targeted attack. Red team exercises and penetration tests fit the bill, but which is right for your organization?

Information security at even well-defended enterprises is often a complex mesh of controls, policies, people, and point solutions dispersed across critical systems both inside and outside the corporate perimeter. Managing that murky situation can be challenging for security teams, many of whom are understaffed and forced to simply check as many of the boxes as they can on the organization’s framework of choice and hope for the best.

Even in a known hostile climate replete with ransomware, sophisticated bad actors, and costly data breaches, security teams are often pressured to deploy tools, coordinate with disparate IT teams, then left to stand guard: monitoring, analyzing, patching, responding, and recovering.

This largely reactive posture is table stakes for most defenders, but on its own, it leaves one important question hanging. How well will all these defenses work when bad guys come calling? Like an orchestra of talented musicians that have never had a dress rehearsal, or a well-conditioned team of athletes that have never scrimmaged, it’s difficult to know just how well the group will perform under real-world conditions. In information security in particular, organizations are often unsure if their defenses will hold in an increasingly hostile world–a world with endless vulnerabilities, devastating exploits, and evolving attackers with powerful tools and expanding capabilities.

Security’s Testing Imperative

At its heart, effective security infrastructure is a finely engineered system. Optimizing and maintaining that system can benefit greatly from the typical engineer’s inclination to both build and test.  From bird feeders to bridges, sewing machines to skyscrapers, no industrial product survives the journey from design to production without being pushed to its limits – and beyond – to see how it will fare in actual use. Tensile strength, compressive parameters, shear forces, thermal capacity, points of failure, every potential weakness is fair game. The concept of stress testing is common in every engineering discipline. Security should be no exception.

Security systems aren’t subjected to blistering heat, abrasive friction, or crushing weight, of course. But the best ones are regularly probed, prodded, and pushed to their technical limits. To accomplish this, organizations turn to one of two core testing methodologies: the traditional penetration test, and the more robust red team exercise. Both penetration testing and red teaming are proven, well-documented approaches for establishing the effectiveness of an organization’s defenses,

Determining which one is best for a particular organization comes down to understanding how penetration tests and red team exercises work and how they differ in practice, core purpose, and scope.

Penetration Testing: Going Beyond Vulnerability Assessment

Penetration Tests (“pentests” for short) are a proactive form of application and infrastructure security evaluation in which an ethical hacker is authorized to scan an organization’s systems to discover weaknesses that could lead to compromise or a data breach.   The pentester’s objectives are to identify vulnerabilities in the client environment, exploit them to demonstrate the vulnerability’s impact, and document the findings.

Penetration testing is generally considered the next step up from traditional vulnerability assessments. Vulnerability assessments – usually the product of software-driven, automated scanning and reporting – expose many unaddressed weaknesses by cross-referencing the client’s systems and software with public lists of known vulnerabilities. Penetration testing takes the discipline a step further, adding the expert human element in order to recreate the steps a real cybercriminal might take to compromise systems. Techniques such as vulnerability scanning, brute-force password attacks, web app exploitation, and social engineering can be included in the test’s stated parameters.

Penetration tests are more targeted and deliver a more accurate list of vulnerabilities present than a vulnerability assessment. Because exploitation is often included, the pentest shows client organizations which vulnerabilities pose the biggest risk of damage, helping to prioritize mitigation efforts. Penetration tests are usually contracted with strict guidelines for time and scope — and because internal stakeholders are generally aware the pentest is taking place — provide little value for measuring detection and response and provide no visibility into the security posture of IT assets outside the scope of the examination.

Penetration Testing in Action

Traditional penetration tests are a go-to approach for organizations that want to immediately address exploitable vulnerabilities and upgrade their approach beyond static vulnerability scanning. Pentests provide valuable benefits in use cases such as:

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