Types of Penetration Testing


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Many organizations have been a potential target to cyber-attacks in the recent days. This has given a rise in demand of penetration testing. Penetration testing attempts to exploit weaknesses or vulnerabilities in an organization’s systems, networks, human resources, or physical assets to stress test the effectiveness of security controls. A penetration test may be performed externally or internally to simulate different attack vectors.

In this article, I am going to explain the different types of penetration tests and why they should be performed. By the end of this article, you will have a better understanding of why penetration tests are an effective layer of defence for any successful cybersecurity program. However, before we dive into the different types of penetration testing, let us first explore what a penetration test is.

What is a Penetration Test?

A penetration test involves a team of security professionals who actively attempt to break into your company’s network by exploiting weaknesses and vulnerabilities in your systems. Penetration testing may include several methods such as using social engineering techniques to access systems and related databases, sending phishing emails to access critical accounts, or using encrypted passwords shared on the network to access sensitive databases. These attempts can be far more intrusive than a vulnerability scan and may cause a denial of service, increased system utilization, reduction in productivity, and corruption of the machines.

Depending on the goals of each test, a penetration tester may or may not have prior knowledge of the environment and systems they are attempting to breach. This is categorized as a black box, white box, and grey box penetration testing. And the different types of penetration testing include:

  • Network Services Penetration Testing
  • Web Application Penetration Testing
  • Wireless Penetration Testing
  • Client-Side Penetration Testing
  • Social Engineering Penetration Testing
  • Physical Penetration Testing

Let us now understand about each type of penetration testing.

Network Services Penetration Testing

Network services penetration testing or infrastructure testing is one of the most common types of penetration testing performed. The primary purpose of this penetration testing type is to identify the most exposed vulnerabilities and security weaknesses in the network infrastructure, including servers, firewalls, switches, routers, printers, workstations, and more of an organization before they can be exploited. The network penetration tests should be performed to protect the business from common network-based attacks, including:

  • Firewall misconfiguration and firewall bypass
  • Router attacks
  • Database attacks
  • SSH attacks
  • IPS or IDS invasion attacks
  • DNS level attacks such a zone transfer attacks or switching or Routing based attacks
  • Proxy server attacks
  • Unnecessary open ports attacks
  • Man-in-the-middle attacks
  • FTP or SMTP-based attacks

As the network of an organization provides mission-critical services to the business, it is recommended that every year, both internal and external network penetration tests be performed at least once. This will give the company with adequate coverage to protect against these attack vectors. Network service penetration testing usually aims to discover the weaknesses and loopholes related to an organization’s network infrastructure. It involves testing DNS attacks, firewall configuration bypass, testing stateful analysis, and many others. And some of the most common software packages which you should examine in this test include secure shell, which is SSH, then you have SQL Server, MySQL, and SMTP protocol, which is a simple mail transfer protocol, then there is file Transfer Protocol. Basically, all the software packages are checked for any loopholes or weak points.

Web Application Penetration Testing

Web application penetration testing is used to identify vulnerabilities or security weaknesses in web-based applications and software such as Google Chrome, Internet Explorer, Gmail, etc. . It uses different penetration attacks and techniques in order to break into the web application. The scope for a web application penetration test includes web-based applications browsers and their components such as Silverlight scriptlets, Activex plugins,  and applets. These types of penetration tests are far more targeted and detailed and therefore are considered to be a more complex tests.

In order to perform web application penetration testing successfully, you must identify all the endpoints of the web-based applications that interact with the user on a regular basis. This work requires a lot of time and effort, from planning to executing the test and finally compiling a useful report. The techniques used in web application penetration testing are evolving continuously with time because of the increase in threats coming from web applications every day. This is the key reason for performing a web application penetration test and identifying security weaknesses or vulnerabilities within web-based applications and their components like database, source code, and the back-end network.

Such penetration tests also help by prioritizing the determined weaknesses or vulnerabilities and provides possible solutions to mitigate them. In software application development, it is considered best practice to improve the code base continuously. Deploying an agile and secure code is the phrase often used to describe this practice. Over large batch deployments, agile code development is the preferred method because the more variables get introduced into the code in a single deployment, the more opportunities there are to create errors or bugs leading to security vulnerabilities.

Wireless Penetration Testing

Wireless penetration testing is performed to identify and examine the connections between all the devices connected to the business’s Wi-Fi. So as the name implies, this test involves examining all the wireless devices which are used in cooperation, and it could be notebooks, tablets, smartphones, laptops, etc. Basically, this test spots weak points in terms of wireless access points, admin credentials, and wireless protocols. A wireless penetration test is typically performed on-site as the pentester needs to be in the range of the wireless signal to access it. Alternatively, a NUC and Wi-Fi pineapple can be deployed onsite to perform the tests remotely. Wireless communications are an invisible running service that allows data to flow in and out of the network, therefore your wireless network should be secure from any vulnerabilities like data leakage or unauthorized access. It would be best if you considered the following questions before performing a wireless penetration test:

  • Have all access points been identified?
  • How many access points are having inferior encryption methods?
  • Is the data flow in and out of the network encrypted, and if so, how? Does the organization have monitoring systems in place to identify unauthorized users?
  • Is the organization using the WPA protocol for all the wireless access points?
  • What are the possibilities that the IT team could have misconfigured a wireless network?
  • What are the preventive measures put in place by the administrators to protect the wireless network?

Social Engineering Penetration Testing

Social engineering Penetration Testing involves attempting to get confidential or very sensitive information by purposely tricking an employee of an organization. Well, you have two subsets here, first, there is remote testing, here you are checking an employee to reveal sensitive information via an electronic means it could be an email or an SMS. Then there is physical testing and this involves the use of physical means to gather sensitive information like maybe you go ahead and threaten an employee or blackmail him to get the information you want, so that’s why it is called physical testing.

According to recent statistics, 98% of all cyber-attacks rely on social engineering because internal users are one of the biggest threats to network security due to how lucrative these scams are. Social engineering tests and awareness programs have proven to be one of the most effective methods of mitigating an attack. For example, KnowBe4, the popular mail phishing platform, simulates an email phishing attack. When the user clicks on a link, they are taken to a page that informs them that it was a phishing test remediation. Training is then provided to help educate and inform users on the most current cyber-attacks and how to avoid them.

Client-side Penetration testing

Client-side penetration testing aims to search and exploit vulnerabilities or security weaknesses in the client-side software programs. For example, putty, email, macromedia flash, adobe photoshop, Microsoft office suite, web browsers that you use such as Internet Explorer, Google Chrome, Firefox. There are vulnerabilities present in those applications as well, so tests are performed to identify specific cyber-attacks, including cross-site scripting attacks, clickjacking attacks, cross-origin, resource sharing, form Hijacking, HTML injection, open redirection, and malware infection.

Physical Penetration Testing

Physical penetration testing simulates a real-world threat whereby a pen tester attempts to compromise physical barriers to access a business’s infrastructure, buildings, systems, or employees. Physical barriers are often an afterthought for most companies, however, if a malicious actor is able to gain physical access to your server room, then they could own your network. Imagine the impact that might have on your business, on your customers, as well as business partnerships. The primary benefit of a physical penetration test is to expose weaknesses and vulnerabilities and physical controls such as locks, barriers, cameras, or sensors. So that flaws can be quickly addressed through identifying these weaknesses. Proper mitigations can be put in place to strengthen the physical security posture.

Final Thoughts

So that was all about different types of penetration testing you must know. Each type of penetration test requires specific knowledge methodologies and tools to perform and should be aligned with a particular business goal. These goals could range from improving awareness of all kinds of cyber-attacks to employees companywide to implementing secure code development to identify flaws and software code in real-time or meeting regulatory or compliance obligations.


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