Exploring the Different Types of Penetration Testing in Cyber Security

When it comes to cyber security, organisations face multiple threats requiring proactive measures to protect sensitive information. One of the most important proactive steps is penetration testing — or “pen testing” — a strategic approach to assessing vulnerabilities and strengthening defences. In our previous article, The 3 Approaches to Penetration Testing: Black, Grey and White Box Testing, we explained the nuances of each approach and the differences and benefits to help you decide which approach best meets your organisation's security needs. 

Although the goal of all pen tests is the same — identifying security gaps to enable them to be proactively addressed — not all systems are alike. As IT environments expand and evolve, new tests emerge to assess new risks, but the same general principles and techniques remain. In this article, we'll introduce you to the six most common types of penetration tests: Network, web application, wireless, physical, insider threat and social engineering pen tests. When executed, each test is further tailored to specific aspects of an organisation's digital and physical security. 

The Need for Varied Penetration Testing  

When conducting a pen test, it is essential to remember that there is no one-size-fits-all test. Risks, environments, and attackers differ across organisations, and the appropriate pen test approach must also consider the maturity level of the organisation’s security posture. Furthermore, no single type of pen test will meet all the requirements an organisation might have. 

Internal vs. External Penetration Testing 

Simply put, an internal penetration test is like performing a security audit of your own home with insider knowledge. Depending on the approach, it can be either a grey box or a white box test. In a grey box scenario, we might be granted limited access — similar to being allowed to enter the home but with minimal information — like plugging into the internal network without additional details. On the other hand, a white box approach provides us full access, such as knowing the floor plan, having the keys to every room, and understanding where valuables are stored. In a world where insider threats and accidental security breaches are a major concern, an internal test ensures your security is rock solid from the inside. 

In contrast, external penetration tests are the digital equivalent of a perimeter check to see how well your organisation’s defences work against external attackers. Just as castles reinforce their walls against outside intruders, your organisation must protect itself against hackers attempting to gain unauthorised access. This type of testing reveals vulnerabilities in your defences that malicious actors could exploit. Strengthening these defences ensures that your publicly accessible resources are protected from attackers. In our Internal vs External At A Glance One Pager, we give you a brief overview of both these services to provide a side-by-side comparison of what each offers. 

Network Penetration Testing 

Network service penetration testing, or infrastructure testing, is one of the most commonly performed types of pen tests. The main objective is to identify exploitable vulnerabilities in networks, systems, hosts and network devices (e.g., routers and switches) before hackers discover and exploit them. Network penetration testing uncovers opportunities for hackers to compromise systems and networks to gain unauthorised access to sensitive data or even take over systems for malicious or non-business purposes. 

Web Application Penetration Testing  

A web application (web app) is an application or programme stored on a remote server and delivered over the Internet through a browser interface. Web services are, by definition, web applications and many, though not all, websites contain web applications. Users can access a web application via a web browser, such as Microsoft Edge, Google Chrome, Mozilla Firefox, or Safari. Web application penetration testing detects vulnerabilities in these web-based applications. Various penetration techniques and attacks are used to uncover potential vulnerabilities.  

Wireless Penetration Testing   

In a wireless penetration test, the connections between all devices connected to the organisation’s Wi-Fi are identified and analysed for vulnerabilities and weaknesses. These devices include laptops, tablets, smartphones and all other Internet of Things (IoT) devices. For many pen testers, 'wireless' used to be synonymous with 'Wi-Fi',” the standard network technology, and many organisations have deployed complex security systems to protect these networks. Today, the term 'wireless' has a much broader meaning, encompassing not only the security of Wi-Fi systems but also that of a range of different proprietary wireless systems such as Bluetooth, Radio Frequency, Zigbee or Z-Wave. 

Physical Penetration Testing 

Physical penetration testing, or physical intrusion testing, is designed to uncover opportunities for malicious actors to compromise physical barriers (e.g., locks, sensors, cameras, keypads, mantraps, etc.) in a way that allows unauthorised physical access to sensitive areas. This can result in data breaches and system/network compromises, as once a malicious actor is inside the building, gaining network access is often easier. 

Insider Threat Penetration Testing 

An insider threat penetration test specifically targets the risks posed by malicious insiders, such as disgruntled employees or compromised contractors. Unlike broader internal testing, this type of assessment is more focused and simulates scenarios where an insider, like an employee with legitimate access, attempts to exploit their position. For example, we might be given access to a company laptop used by a staff member and simulate actions such as trying to access restricted areas like Finance or HR, deleting sensitive documents, or even collaborating with external attackers. This test aims to identify vulnerabilities in your organisation’s internal systems, access controls, and monitoring processes, helping to enhance your ability to detect, prevent, and respond to potential insider threats. 

Social Engineering Penetration Testing 

Social engineers are hackers who exploit a weakness found in almost every organisation: human behaviour and psychology. These attackers use various tactics, including phone calls, social media, and especially e-mail, to trick people into granting access to sensitive data or other company resources. In social engineering tests, a malicious actor tries to persuade or trick users into giving them confidential information, such as usernames and passwords.  

Choosing the right Security Provider for your Organisation  

Penetration testing is one of the best ways to assess the robustness of your cyber security defences. However, to reap maximum benefits, penetration tests must be correctly managed. It's essential to select a team with extensive industry experience, a plan for securing your data during testing, methodologies based on industry best practices, and sample reports for your review.  

Having the right penetration testing partner could be the difference between the success and failure of your endeavour. If you plan to conduct the penetration tests collaboratively, include at least two external cyber security experts on the penetration testing team. An independent, external opinion is essential to avoid blind spots. When selecting external vendors, keep the following tips in mind: 

• Assess the credentials, experience, and expertise of the external provider and each penetration testing team member. Each team member should have experience across various industries and organisations of all sizes and hold the requisite certifications. 
• Understand how the penetration testers will protect your data during and after the test. Define and agree on how confidential data will be transferred, stored, and destroyed. 
• Review the methodology your provider will use. It must be based on industry best practices and include automated and manual testing methods. 
• Ask your provider for sample reports. Assess whether the reports are clear, easy to understand, and contain risk-prioritised recommendations. 
• Ensure your provider offers retesting to verify your remediation efforts. Retesting is critical in the continuous penetration testing process. 

At Cyberlogic, we offer a comprehensive suite of cyber security solutions, which includes penetration testing, vulnerability management, and remediation solutions. To find out more, visit the Security Solutions page on our website or reach out to us at hello@cyberlogic.co.za.