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Put vulnerability management to the test — the penetration test

July 14, 2023 Article 6 min read
Joe Oleksak Mike Lipinski Andrea Selke
A strong vulnerability management program is paramount to your organization’s information security and its resilience. Penetration testing assesses whether this crucial control is operating effectively — an important consideration for leaders and C-suite stakeholders across your organization.
Business professional standing next to a glass windowA well-established vulnerability management program — characterized by proactive identification, thorough assessment, and effective mitigation of vulnerabilities before they’re exploited by malicious hackers — plays a crucial role in enabling organizations to promptly detect and prevent cyberattacks. But how do you know if this critical control is working?

How penetration testing works

In contrast to a vulnerability management program that functions as a control, a penetration test (pen test) serves as a comprehensive evaluation of the effectiveness of your organization’s vulnerability management program and its broader cybersecurity initiatives. Penetration testers use a diverse range of tools and techniques to gain valuable insights into your environment, replicate potential “attacks” to infiltrate your users, systems, and network, and gain access to sensitive data. Their primary objective is to identify any “unlocked doors and windows” within your IT systems, specifically those that you may think are fortified against malicious intrusions. Once penetration testers successfully breach your defenses, they then look to uncovering any gaps or misconfigured system or application settings that could potentially allow actual hackers to exploit sensitive information flowing through your network. This can include passwords and protected customer or patient data, as well as critical financial details like credit cards and banking information.

Not all penetration tests are equal

Penetration testing is a rigorous and comprehensive process that goes beyond evaluating technology alone. It encompasses the assessment of people and processes, including technical, social, and physical vulnerabilities. While there may be free tools or scans available that claim to fulfill this role, it’s essential to recognize their limitations. Automated systems alone can’t account for the myriad variables and real-life scenarios that create potentially significant vulnerabilities. When our team conducts pen tests, we meticulously examine weaknesses in technology while also scrutinizing social and physical vulnerabilities that put an organization at risk.

When our team conducts pen tests, we meticulously examine weaknesses in technology while also scrutinizing social and physical vulnerabilities that put an organization at risk.

For example, our testers have successfully employed social engineering tactics — such as cloning access badges during staff breaks — and gained physical access to buildings. This allowed us to discreetly plant malicious devices, enabling wireless network attacks from unexpected locations like a parking lot.

In another case, a client relied on end-point protection measures, which secure entry points of devices such as desktops, laptops, and mobile devices, to safeguard their network, which initially posed a challenge for our penetration testing team. However, through identifying a configuration weakness, we successfully gained access to their network. From there, we assessed how they might identify or prevent the unwanted transfer of data. Rather than removing actual data, we used test data structured in a similar manner to represent the sensitive information a hacker would try to exfiltrate. This comprehensive evaluation allowed us to identify potential weaknesses and gaps in the defensive measures implemented by the organization.

When we share with business leaders and IT directors that we’ve successfully gained access to their network — sometimes even acquiring high-level credentials — their reaction is often one of surprise and astonishment: “I can’t believe my people would click that link,” “I can’t believe the vendor overlooked that configuration change,” “I can’t believe our vendor failed to patch the system,” or “How could our employees use such weak passwords?”

These surprises usually arise due to procedural gaps within the organization. Information and cyber security require more than just technological controls — they extend to people and processes across the entire organization, as well as external collaborators. While your IT team diligently works to secure the organization by implementing controls around technology, it’s impossible for them to have complete knowledge in all areas. To build an effective vulnerability management program, you need to identify and address the vulnerabilities that may go unnoticed. This is precisely what penetration testing uncovers — the vulnerabilities that both you and your IT team might not be aware of.

While automated network access tools might scan and halt our efforts, we emulate the tenacity of real hackers who persist until they’re successful. By considering the interplay of technology, social engineering, and physical security, we ensure a thorough assessment that automated tools and vulnerability scans just can’t replicate.

Pen testing results and remediation

Using targeted findings and industry-standard recommendations obtained through a pen test, organizations learn precisely where the gaps are in their vulnerability management program. This valuable information allows IT to enhance the organization’s controls. But it’s equally important that C-level executives are involved; they play a significant part in the success of information security and remediation efforts following a comprehensive penetration test. As stewards responsible for the overall resilience of the organization, executives play a vital role in supporting IT in effectively addressing vulnerabilities. Their involvement ensures IT has the resources it needs to implement targeted remediation strategies based on the pen test findings. By actively participating in the remediation process, C-level executives demonstrate their commitment to establishing a robust and mature information architecture, instilling a culture of cybersecurity throughout the organization.

IT directors often use the findings from pen testing to strengthen their case for increased budgets, whether it be for technical improvements or user training. We understand that budget increases for your cybersecurity program might not always be practical. But by prioritizing cybersecurity, you can position your organization — with considerable success — to be less vulnerable and less of a target for potential attacks.

What types of organizations should have a pen test, and how often?

It’s a common misconception we hear frequently: “We’re just a nonprofit, a family-run business, a community hospital, a local utility, a middle-market manufacturer ... no one’s going to attack us.” Unfortunately, this often comes back to haunt organizations. While it’s true that different organizations are targeted for various reasons by a wide range of attackers who use diverse tools, including artificial intelligence, to gain unauthorized access or control, or pilfer credentials, funds, patient information, or data, the reality is that every organization is vulnerable.

Moreover, the landscape of cybersecurity has evolved, with many cyber insurers now mandating penetration testing as a prerequisite for coverage. Furthermore, numerous standards and regulatory compliance frameworks such as ISO, NIST, HITRUST, and others require independent third-party testing. Customers are also increasingly demanding that their service providers undergo pen testing to assess the overall effectiveness of the provider’s vulnerability management programs.

In most cases, we recommend organizations conduct pen testing on an annual basis, or even more frequently if there’s a need to verify remediation efforts from a previous test or a breach. Vulnerabilities emerge and evolve constantly, alongside the increasing sophistication of attackers and their toolsets. Like your vulnerability management program and overarching cybersecurity strategy, pen testing should be a proactive and continuous endeavor.

By regularly performing penetration testing, you gain the ability to identify gaps in people, processes, and technologies, ensure your systems can detect and thwart hackers, and monitor for emerging vulnerabilities. Neglecting routine pen testing — meaning, at the very least, conducting it annually — exposes your organization to unnecessary risks. It’s simply impossible to establish effective controls for information security issues that remain undiscovered.

It’s simply impossible to establish effective controls for information security issues that remain undiscovered.

The significance of a robust vulnerability management program cannot be overstated, particularly if you’re responsible for the overall resilience of your organization. It’s crucial to know whether your cybersecurity program is operating effectively, and pen testing is the most reliable tool for assessing the performance of one of your organization’s most critical controls.

Think cybersecurity is just an IT responsibility? A holistic approach to cyber is critical for your organization. 

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