In the world of cyber security, it’s possible to do everything right on the surface, and still get attacked by a malicious cyber hacker. How is this possible?

While being one of the most effective means of protecting your business from cyber threats, penetration testing is not without its flaws. The problem doesn’t lie in the tests themselves, but rather, in how thorough the penetration testers are. Unfortunately, you can’t eliminate the risks entirely, you can only minimize them.

You can’t know what you don’t know. That’s the main reason why penetration testing can fall short. To help you conduct the most thorough tests, and prepare for an instance where pen testing does fail you, we wrote this article about the limitations of penetration testing. At EliteSec, we have years of experience running penetration tests and creating security measures to insulate companies from the actions of hackers.

What Is Penetration Testing?

Penetration testing (pen testing) is a type of simulated attack that accounts for all the different ways your cybersecurity defenses (the target system) can be taken advantage of. Essentially, a penetration tester will behave the same way as a hacker, and attempt to gain access to the target system in as many ways as possible. Once the tester enters the target system, they will do everything they can to become an administrator in your system and gain the ultimate form of control over it. Gaining and maintaining access is at the heart of every penetration testing strategy. This process requires not only a roundup of the system’s security vulnerabilities but also careful strategic planning to exploit them. A vulnerability scan is merely the first step in a penetration test, rather than being the end-all and be-all. Therefore, pen tests don’t just show your system’s potential flaws, they show you exactly how they can be exploited. This helps you optimize your defense systems and develop effective incident response plans in case there is a breach.

Why Is Pen Testing Important?

Practically any business that handles a large amount of user data can benefit from a pen test. After all, protecting user data is integral to protecting your reputation. If you store large amounts of data, there is bound to be some opportunistic hacker that wants access to it. In the case of a breach that affects dozens of users, your name is sure to be tarnished by some publication. Cyber security is about building trust with both current and potential clients, and the amount of money you lose just from negative PR can far exceed the cost of repairing the damages to your cyber security systems.

Moreover, some industries, such as financial, health, and education, have special standards for data protection. These regulations are essential to lawfully operating your business in Canada, the United States, and beyond.

Where Pen Testing Falls Short: The Blind Spot Dilemma

While Informa Tech found that most large enterprises, with 3000 or more employees, conduct penetration tests, only 38% of those organizations test more than half of their attack surface on a yearly basis. That means that most major companies and institutions are leaving vast swathes of customer data at risk. Their attack surface includes things like web applications, networks, hardware, interfaces, and even people (through social engineering).

Pen testing isn’t just about checking a box and forgetting about it. Your pen tester should be conscious of the decisions that they are making concerning what they test and how they test it. Neglecting to prepare for things like social engineering attacks, where an individual attempts to talk their way into your system, is a common mistake that organizations and pen testers make. That’s why your pen tester needs to consciously account for every single attack vector first and test it. It can be an arduous process, but it’s far superior to leaving things up to chance.

However, a bit of laziness or lack of focus on the part of the pen tester can create massive blind spots to be exploited down the road.

What’s At Stake?

One survey noted that while major enterprises had over 10,000 assets connected to the internet, the majority said that fewer than 1,000 (or 10% of those assets) were actually attacked during the penetration testing process.

That’s a lot of attack vectors for a hacker to choose from. It could be said that many organizations don’t just have a blind spot, they have a gigantic blind stain that covers most of their company.

Where Do These Blind Spots Come From?

Look, penetration testing is one of your best weapons in a cybersecurity strategy. However, it’s hardly the end all and be all. Overreliance always brings drawbacks and blind spots like the ones we just described.

Limits In Technology

At this point, cyber hackers are well aware of the fact that you are using penetration tests. As such, they’re constantly improving their tactics and devising new strategies that allow them to go undetected as they enter your system. These are called “zero-day vulnerabilities” i.e., you have no protection against them because penetration testing relies on known attack vectors and types. Successful cyber-attacks often come from the hacker who has the most skills and imagination. And it’s not just new tactics, it’s also new malware.

Pen testers who use outdated technology and techniques in their methods are also putting your sensitive data at risk. These tools often fail to account for the evolution of cyber attacks and malware in recent years.

Limitations In Scope

We already mentioned that most companies leave their attack vectors wide open as the majority of their online assets are not protected during penetration tests.

But it’s understandable why a company would decide to operate this way. After all, pen tests are time-consuming and can use up valuable resources that a company would prefer to deploy elsewhere. Reducing network availability for your users is bound to frustrate them and hamper your daily operations.

Penetration tests can take anywhere between 1 week and 1 month, depending on the number of attack surfaces and the size of your organization. This begs the question, how could you possibly conduct a monthly pen test if it takes an entire month to complete one? It would be like traversing a highway that permanently has a couple of lanes closed off due to construction. This greatly reduces your organization’s efficiency, which prevents your business from reaching the targets it needs to grow.

Gaps Between Pen Tests

Since pen tests are seen by many industries as an obstacle to growth, many organizations will fail to run them as extensively and frequently as they could, simply because they don’t want to deny service to their users too often.

45% of companies only run pen tests once per year, and 27% run them every quarter, it’s clear that within a few weeks or months, you could leave yourself vulnerable. The issue is the same as always, pen tests don’t predict what new attacks could be devised between now and your next pen test. Even as nearly 80% of companies believe that penetration testing is too costly, the costs of a cyber attack will be much worse. The more frequently you run pen tests, the more likely you are to keep abreast of new cyber threats.

Human Error And Lack Of Expertise

While there are many competent pen testers available on the market, hiring one full-time can be too costly for an organization. Plus, considering what we said earlier about how constantly running pen tests creates a bit too much friction for a modern organization, you would be best advised to pursue a part-time one.

Of course, some organizations neglect to hire a pen tester altogether and might delegate the penetration testing role to an already overworked IT team. The fact that cyber threats are extremely nuanced makes shuffling the burden of pen testing to others in your organization an extremely irresponsible move. Automated tools can help fill this gap, however, there is nothing like a well-carried-out manual pen test that accounts for every attack surface in-depth.

How To Counter Your Blind Spots

So, given these limitations of penetration testing, what is the average company to do? There is a bit of a principle-agent problem here. Since you might not be a pen testing expert, you might not know whether your pen tester will actually do a thorough job. That’s why it is best to involve your IT team or other trusted individuals who are familiar with your security assets in the process of selecting a penetration tester.

However, there are still further measures that you can take to upgrade your penetration testing and security testing in general. Here are a few of them.

Frequent Testing

You’re already aware of the massive costs, both financially and logistically, of running frequent pen tests. However, can you really put a price on the reputation of your company? Depending on your industry regulations and the number of potential threats, you can reach out to a pen tester to ask them about how often you should conduct pen tests in your industry.

Regular Updates And Upgrades

Software platforms, applications, and systems are dynamic entities, consistently evolving and adapting. Whichever software or security tools your organization employs, it is imperative to ensure that they are updated and upgraded at regular intervals. This process isn’t just about incorporating new features but is fundamentally an effort to patch known vulnerabilities and bolster the security infrastructure.

In many cases, cybercriminals are quick to exploit known vulnerabilities in outdated software, making organizations easy targets for data breaches and other cyber-attacks. Thus, regular updates and upgrades act as a proactive measure to counter potential security threats, providing a solid foundation for your cybersecurity strategy. Furthermore, it ensures compatibility with other evolving technologies and compliances, maintaining the optimal performance and security levels of the systems.

Leveraging AI Tools

In a bid to counter the blind spots that traditionally plague penetration testing efforts, leveraging Artificial Intelligence (AI) tools has surfaced as a promising strategy. These tools can seamlessly analyze a plethora of data, identifying patterns and anomalies that might escape the human eye. In terms of penetration testing, AI tools can effectively simulate various cyber-attack strategies, predicting potential vulnerabilities with high precision and speed. This can be much more dynamic than a human penetration tester, as they can adapt and learn from the data they process, thus becoming progressively better at identifying potential threats. That said, even if AI tools can operate round the clock, they still require some human intervention.

Peer Review

Inviting a fresh pair of eyes to review the penetration testing strategies and results can be a potent method to counter blind spots. Peer review involves having another team or expert - outside the initial group that conducted the tests - to review and evaluate the testing process and findings. This can help in identifying any oversights or errors, and provide new perspectives on potential vulnerabilities that might have been missed. This also helps resolve the principle-agent problem we mentioned earlier.

Peer reviews facilitate a culture of collaboration and knowledge sharing, which can be invaluable in addressing the complex and evolving cyber threats. By encouraging diverse opinions and insights, peer reviews can foster a more comprehensive and effective approach to penetration testing, minimizing the risk of blind spots and ensuring that the testing process is thorough and well-rounded.

Comprehensive Training

To effectively counter the blind spots in penetration testing, comprehensive training programs must be instituted. These programs should not only focus on equipping your teams with the latest skills and knowledge in the field but also foster a culture of critical thinking and problem-solving. In a table-top exercise, a tester simulates real-world scenarios and case studies, encouraging the teams to think like attackers and anticipate various strategies that might be employed to exploit the system’s vulnerabilities.

Furthermore, training programs encourage continuous learning and development, considering the dynamic nature of the cybersecurity landscape. This could include workshops, seminars, and collaborations with experts in the field, ensuring that the teams are constantly updated with the latest trends and developments.

Create Holistic Security Assessments

To truly hedge against the potential blind spots in penetration testing, organizations should aim to create holistic security assessments that encompass a wide spectrum of vulnerabilities, both apparent and latent. Expert teams like ours at EliteSec specialize in crafting comprehensive security assessments that delve deeply into various facets of an organization’s security landscape. These encompass not only the digital domain but also consider aspects like human factors and physical security measures, thus offering a 360-degree view of the potential vulnerabilities.

Incident Response Planning

In mitigating the blind spots encountered in penetration testing, structured incident response planning plays a crucial role. This strategy ensures that your organization is prepared to act swiftly and efficiently in the event of a security breach, helping to minimize damage and accelerate recovery.

To plan properly, you must leverage the data and insights derived from penetration testing to develop a blueprint that maps potential vulnerabilities and prepares for possible exploitation. It makes you adept at handling every facet of a breach, including legal compliance and public relations, thereby ensuring your organization is primed to manage the repercussions of a security breach seamlessly, preserving both integrity and public trust.

Consult EliteSec To Counter Cybersecurity Blind Spots

If there’s one lesson you should take from this article, it’s that cyber security is an extremely nuanced field. Penetration testing connects to many aspects of your business. As such, you should choose a penetration tester that has a comprehensive view of cyber security. One that can also assist with training your employees to follow cybersecurity protocols or picking effective security software.

With these skills in hand, EliteSec is the ideal choice to handle penetration testing and any other cyber security services you require. We can help reinforce your business' cybersecurity posture so that you can protect your data assets and your reputation, and set your team up for continued success.

We’re happy to offer you a free 30-minute consultation where we’ll run through these pressing issues over video chat. Check out our availability to book an appointment.