A surprise they weren’t prepared for, and in hindsight, they’ll tell you that they wish they had prepared.

At the company level, cyber attacks often come as a shock too. Fortunately, there are a lot of things that a company can do to prepare for a cyber attack. And in the realm of cyber security, penetration testing stands out as one of the top ways to hinder future cyber attacks. The cyber security philosophy behind penetration testing is that it’s better to be proactive than reactive.

This article from EliteSec will give you an overview of penetration testing and its role in your cyber security posture. By the end, you’ll understand how penetration testing works, how it can benefit your company, and what circumstances this testing can be deployed in.

What Is A Penetration Test?

Penetration testing is, in essence, a secure simulation of the activities hackers perform when they attempt to gain access to your systems. In this case, the penetration tester is not a hacker, rather they are a trusted cybersecurity expert hired by a company to break into their hardware and software, essentially, any device or tool that you have that faces the internet.

Here are some concrete examples of what penetration tests do to ameliorate your company’s security posture and protect its sensitive data.

Identify Vulnerabilities

While conducting their tasks, pen testers will attempt to exploit potential security gaps, such as unpatched software, weak passwords, or misconfigured systems, to assess what kind of unauthorized access or harmful activities could be possible.

Assess Your System’s Resilience

By carrying out a thorough overview of your security weaknesses and testing each one, they’ll also observe where your internal systems were able to hold up. Particularly when evaluating the effectiveness of internal defense mechanisms and protocols.

Ensure Organizational Compliance

Depending on your industry, there could be a whole host of industry standards that your organization’s systems must comply with to operate in Canada and the rest of the world. If you’re in the financial, healthcare, or educational industry, you’ll likely have to comply with particular standards. For example, the PCI DSS for payment card security or HIPAA for healthcare data.

Breaking Down The 5 Phases Of Pen Testing

Reconnaissance

For pen testers, this is the information-gathering stage. They’ll use every tactic at their disposal to learn more about your computer system. And the research tactics aren’t just limited to the internet. Some pen testers have been known to conduct social engineering attacks to obtain information about your systems. That means they’ll attempt to pose as someone your company trusts to gain vital information they need to exploit the target system.

Scanning

This stage, also known as “vulnerability scanning”, often gets confused with the entire pen test itself. This would be incorrect because vulnerability scanning only allows the pen tester to identify some of the potential attack vectors that hackers could use.

Pen testers will use automated vulnerability scanning tools to search for things such as open ports, weak encryption, outdated software, or misconfigurations.

Gaining Access

Once the vulnerability scan is complete, the pen tester has a list of potential attack vectors. Plus, they have enough information about your systems to ideate novel ways to penetrate into your system.

The tactics the pen tester uses to gain access to your security infrastructure are highly varied. For instance, a pen tester could use code injection, malware, or dozens of other options. Their choice will depend on your weaknesses and what they think is best. They’re putting themselves in the shoes of a hacker and trying to find every potential avenue.

Maintaining Access

In a real attack, any hacker would try to stick around as long as possible to exploit whatever they can. Similarly, the pen tester uses their skills to escalate the attack. They might attempt to gain administrative privileges over your system. Or, they could create backdoors that could be used by a hostile party later. This will give you a full account of the vulnerabilities your system has, and some clues on how to fix them.

Analysis & Reporting

Now that the tester has compiled all the data, they can begin sorting out exactly where things went wrong, how they went wrong, and how you can improve. This will form the focal point of your future cybersecurity endeavours as a team. The pen tester will debrief your IT team on their activities and recommend a course of action to pursue, including prioritizing your vulnerabilities based on severity and potential impact.

How To Decide The Pen Tester’s Access Level

To plan a penetration test, the tester must choose a type of pen testing that grants them a level of access to your systems. It significantly influences the testing approach, depth of the analysis, and the kind of vulnerabilities that can be identified. Let’s look at each testing method.

Black Box Testing

Black Box Testing is when the tester has no prior knowledge of the system’s internal workings. This approach emulates the tactics of an external hacker, with the tester having access only to publicly available information. The pen tester must exclusively discover and exploit vulnerabilities that are visible from an outsider’s perspective. That means they have no insider knowledge of your network, system, or application. This type of testing is a true test of how well a system can defend itself against real-world attacks.

By looking at the organization’s defenses from the outside, this method is particularly effective in uncovering high-level process issues that could be overlooked from an internal perspective. However, one of the drawbacks of this approach is its time-consuming nature, as the tester has to start from scratch without any prior knowledge. Furthermore, Black Box Testing may not thoroughly identify internal vulnerabilities or deep-seated security issues, which might remain undiscovered due to the lack of internal system access.

White Box Testing

On the other hand, White Box Testing provides the penetration tester with comprehensive knowledge of the system. In this scenario, testers are given full access to your critical system components, including source code, architecture diagrams, network infrastructure details, and credentials. This allows you to uncover vulnerabilities that may not be apparent or accessible from an external point of view.

While White Box Testing is the most comprehensive type of testing, one limitation of this method is that it might not accurately simulate the perspective of an external attacker, which is what you’re ultimately preparing for. White Box Testing is particularly well-suited for detailed security auditing, compliance verification, and in-depth analysis of internal security protocols.

Gray Box Testing

Gray Box Testing represents a hybrid approach, blending elements of both Black Box and White Box Testing. In this method, the penetration tester possesses limited knowledge about the system—more than in Black Box Testing but less than in White Box Testing. For instance, this might include some network or system information, but not the full details of the system’s internal workings. This, of course, could be representative of a social engineering attack, where a hacker has obtained some limited knowledge of your system but doesn’t see the full picture. They still act as an authentic external threat, but the approach is a little more balanced, especially if there is a particular internal weakness that needs to be highlighted.

The Different Attack Surfaces Involved In Pen Testing

Your computing infrastructure is likely vast. Penetration testing services must examine every potential attack vector imaginable, including the following.

Network Infrastructure

Network Infrastructure includes routers, switches, firewalls, and other networking equipment. Penetration testers probe these components for vulnerabilities such as weak encryption, open ports, and misconfigured firewalls, which are critical in maintaining the overall security of the network.

Web Applications

Websites and web applications are common targets in penetration testing. Testers look for security issues like SQL injection, cross-site scripting (XSS), and other vulnerabilities that can be exploited to manipulate or steal data from these platforms.

Mobile Devices and Applications

With the rise of smartphones and tablets, mobile platforms have become significant attack surfaces. Security assessments focus on vulnerabilities in both the devices and their applications, including insecure data storage, weak authentication, or exposure to mobile-specific attacks.

Cloud Services and Storage

As cloud-based services become more prevalent, their security becomes increasingly important. This includes assessing vulnerabilities in Software as a Service (SaaS), Platform as a Service (PaaS), and Infrastructure as a Service (IaaS) models, ensuring that data and services hosted in the cloud are secure.

Internet of Things (IoT) Devices

IoT devices, such as smart thermostats, security cameras, and smart appliances, are often connected to networks and can be underrated security risks. Penetration testers focus on identifying unsecured endpoints, lack of encryption, and other vulnerabilities in these devices.

End-User Devices

This category includes desktops, laptops, and other personal computing devices used within an organization. Penetration testing in this area targets vulnerabilities that can be exploited through phishing, malware, or unsecured remote access.

Containers

Containers like Docker and Kubernetes are easily exploitable if not secured properly. If your containers are misconfigured, pen tests will help reveal this flaw.

Email Systems and Servers

Email systems are frequent targets for attackers. Penetration testing in this domain focuses on identifying vulnerabilities that could allow spam, phishing attacks, or unauthorized access to sensitive communications.

APIs

APIs facilitate communication between different software applications and are crucial attack surfaces. Security testing in this area focuses on matters like insecure endpoints, lack of authentication, and improper authorization checks in APIs.

Wireless Networks

Wireless technologies such as Wi-Fi and Bluetooth have their own set of vulnerabilities. Testing focuses on identifying weaknesses in encryption, unauthorized access, and vulnerabilities in wireless protocols.

Data Storage and Databases

This area involves ensuring the security of stored data, whether on-premises or in the cloud. It’s critical to protect data storage and databases from unauthorized access, tampering, or loss, ensuring the integrity and confidentiality of the data.

Employee Behavior and Social Engineering

The human element, such as employee behavior, can also pose threats to your security system. Security professionals might deploy social engineering tactics to assess the susceptibility of your personnel to phishing, pretexting, tailgating, and other similar threats.

What Types Of Penetration Testing Tools Should You Use?

Penetration testers use quite a catalogue of tools. These can range from reconnaissance tools that help them research your system, all the way up to unique tools that help them hack into it. Typically, it’s up to the penetration tester to decide on which tools they want to use, but we wrote a full article on 12 different tools pen testers us to give you an idea.

In general, we can separate pen testing tools into 4 categories:

• Information-gathering tools, to help you with the research side of the process.
• Exploitation tools, to help you exploit your security systems and your network.
• Vulnerability scanning tools, to help you account for vulnerabilities.
• Comprehensive tools, which complete multiple steps for you giving you a holistic view of things.

Fitting Penetration Testing & Cybersecurity Together

We’ve talked a lot about penetration testing. However, you should understand that it is not a standalone solution but rather, a significant part of a comprehensive cybersecurity strategy.

Integrating penetration testing into your broader cybersecurity efforts brings several benefits. It allows you to pinpoint specific weaknesses in your defenses, offers insights into the potential impacts of different types of cyber attacks, and helps in prioritizing security improvements.

But once you’re finished with the pen testing work, you still need to deploy threat intelligence, monitor your defenses, plan incident response, and educate your user base. The insights given to you by the pen tester must be implemented in practice.

For all your penetration testing needs, our cybersecurity team at EliteSec can assist. Not only will we integrate the pen testing into your wider security posture, but we’ll also give you an honest assessment of what your needs are at this time. Schedule a free 30-minute consultation to get started.

Frequently Asked Questions

What Is The Goal Of Penetration Testing?

A penetration test has 3 goals. The first is to identify your vulnerabilities so that they can be rectified in the future. The second is to evaluate how strong your existing security approach is so that you can accurately recommend upgrades. The third objective of penetration testing is to comply with security standards in your field, including HIPAA and the PCI-DSS, as industry-specific examples for health and eCommerce respectively. Each of these helps you fortify your cybersecurity posture.

Who Performs Penetration Testing?

Penetration testing is typically performed by specialized cybersecurity professionals known as penetration testers, they can also be described as ethical hackers. They possess a deep understanding of computer systems, networks, and software, along with the tactics used by malicious hackers. Penetration testers can be internal employees of the organization, part of a dedicated security team, or external consultants hired specifically for their expertise in pen testing. External testers often bring an unbiased perspective and specialized skills, while internal testers have a more intimate knowledge of the organization’s systems.

Is Penetration Testing The Same As Cyber Security?

Penetration testing is a component of cybersecurity, but they are not the same thing. Cybersecurity is a broad field that encompasses a range of practices, technologies, and processes designed to protect networks, computers, programs, and data from attack, damage, or unauthorized access. Penetration testing is a specific tool within this field, focused on identifying vulnerabilities and testing the effectiveness of security measures. It’s one of the many tactics used in cybersecurity to ensure the protection of systems and data. While penetration testing is critical, it works best when integrated into a comprehensive cybersecurity strategy.

Is A Penetration Tester A Hacker?

A penetration tester is often referred to as an “ethical hacker.” However, unlike malicious hackers, who exploit vulnerabilities for illegal or unethical purposes, penetration testers use their skills to identify and help fix security weaknesses. They utilize similar tactics to achieve different results. Ethical hackers are authorized by a company to test their security systems and draw out plans to fortify them. The key difference lies in the intent and authorization; ethical hackers aim to protect and strengthen systems, whereas malicious hackers aim to exploit them.