PenTesting, also known as “ethical hacking” or “white-hat hacking,” has always been viewed as the “sexy” side of cybersecurity, a task that is far more exciting than monitoring systems for intrusions, shoring up defenses, or performing compliance audits.

Numerous security conferences are devoted to the fine art of attempting to hack into systems – with an owner’s full knowledge and permission – and reporting on the results.

At an organisational level within businesses, they also value PenTesting under the premise that it allows them to identify security vulnerabilities before cyber criminals can. There are some regulatory requirements like PCI-DSS that require penetration assessments as part of their PCI compliance.

However, many organisations have come to over-rely on PenTesting, thinking that if all the issues were identified in a PenTest, they’re good to go. Not only is this not helping them improve their security posture, it is also leaving them with a false sense of security.

A penetration test is a simulated, live attack on your environment by a white-hat hacker

What is PenTesting?

A penetration test is a simulated, live attack on your environment by a white-hat hacker, customised to address specific problem areas, such as web-based applications, mobile applications and infrastructure services like border VPNs and firewalls.

The PenTest may include different types of attacks based on the requested scope from an organisation so that the tester attempts to come at each system from all sides, the way a cyber-criminal would. The goal is to identify which systems and data the tester was able to access and how an organisation can address the vulnerabilities that allowed them to get in.

The limitations of PenTesting

There is great value in performing periodic PenTests, which is why PCI DSS and other security standards mandate them. However, PenTesting has three significant limitations:

PenTesting does not provide solutions

Let’s be honest: No one likes reading technical reports, but typically, that's the only deliverable provided by a PenTester. The value of a PenTesting report varies wildly based on the scope of the testing, the PenTester’s technical expertise and their writing ability. The tester may miss some things, or not clearly convey their findings.

Additionally, a PenTest is a snapshot in time and the PenTester could miss changes in the systems, configurations, attack vectors and application environments. Even if your system “passes” a PenTest, will it crumble in the face of a brand new, more powerful attack vector that emerges a week later?

The worst type of “PenTest report” consist of an analyst producing nothing more than the results of a vulnerability scan. Even if the PenTester produces a well-written, comprehensive report filled with valuable, actionable information, it’s up to your organisation to take the action, which leads to the next limitation of PenTesting.

any security issues that are identified during a PenTest aren't validated, which leads to a misrepresentation of their magnitude
The value of a PenTesting report varies wildly based on the scope of the testing, the PenTester’s technical expertise and their writing ability

PenTesters only exploit vulnerabilities and do not promote change

PenTesting does not highlight the missing links in your organisation's technology stack that could help you address your security vulnerabilities. This is often in the guise of being agnostic to the technologies that exist because their expertise is only offensive security – unless, of course, the performing company has “magic software” to sell you.

PenTests also do not help to develop your organisational processes. Additionally, they do not ensure that your employees have the knowledge and training needed to treat the identified fixes. Worst of all, if your in-house expertise is limited, any security issues that are identified during a PenTest aren't validated, which leads to a misrepresentation of their magnitude and severity while giving your team a false sense of security.

PenTesters are self-serving

Too often, PenTesting pits the assessment team against the organisation; the goal of the assessment team is to find the best way to "shame" the business into remediation, purchasing the testing company’s “magic software”, then call it a day.

Once the PenTesters find, for example, a privilege escalation or a way to breach PII, they stop looking for other issues. The testers then celebrate the success of finding a single “flag”. In the meantime, the business is left in a precarious situation, since other unidentified issues may be lurking within their systems.

Shifting the paradigm of PenTesting

The goal of PenTesters is to find the best way to "shame" the business into purchasing the testing company’s “magic software”, then call it a day

Penetration testing can uncover critical security vulnerabilities, but it also has significant limitations and it’s not a replacement for continuous security monitoring and testing.

This is not to say that all PenTesting is bad. PenTesting should be integrated into a comprehensive threat and vulnerability management programme so that identified issues are addressed. The purpose of a mature vulnerability management programme is to identify, treat and monitor any identified vulnerabilities over its lifecycle.

Vulnerability management programme

Additionally, a vulnerability management programme requires the multiple teams within an organisation to develop and execute on the remediation plan to address the vulnerability. A mature threat and vulnerability management plan takes time and is helpful to partner with a managed security services provider (MSSP) to help you in the following areas:

  • Improve your cyber-risk management program so that you can identify and efficiently address vulnerabilities in your infrastructure, applications and other parts within your organisation’s ecosystem on a continuous basis;
  • Perform retests to validate any problems identified through a vulnerability scan or a PenTest assessment;
  • Ensure that your in-house staff has the knowledge, skills and tools they need to respond to incidents.

Cyber risk management and remediation is a "team sport." While periodic testing conducted by an external consultant satisfies compliance requirements, it is not a replacement for continuous in-house monitoring and testing.

To ensure that your systems are secure, you must find a partner who not only performs PenTesting but also has the engineering and development experience to assist you in fixing these types of complex problems in a cost-effective manner and ensuring that your systems are hardened against tomorrow’s attacks.

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Andy Jordan Special Project Lead, Mosaic451

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