What Are the Different Types of
Penetration Testing?

Penetration testing (aka pen testing or ethical testing) involves testing a computer system, network, or web application to check exploitable security vulnerabilities. Pen testing can also be used to test an organization’s security policy, compliance requirements, and its ability to identify and respond to security incidents.


How Often You Should Perform Pen Testing

Pen testing should be performed on a regular basis, preferably once a year. This boosts network security and ensures more consistent IT management. There are other instances where an organization may feel the need to perform pen testing:

● When adding a new network infrastructure or applications
● When making major upgrades or modifications to its infrastructure or applications
● When establishing offices in new locations
● When looking for security patches or modifying end-user policies

Other factors may affect the frequency of performing pen testing, including the company’s size, the cost of pen testing, regulations, and compliance. Pen testing efforts should be customized to the individual organization and the industry it operates within.


The Process of Penetration Testing

The penetration testing process can be broken down into five stages. The first stage involves planning and reconnaissance. Here, the test’s scope and goals are set, including testing methods and systems to be addressed. Useful information like mail servers, networks, and domain names are gathered to help understand potential vulnerabilities.

The second stage involves scanning to understand better how the target application’s code will respond to various attempts to intrude. Static analysis inspects an application’s code to estimate the way it responds while running. Dynamic analysis provides a real-time view of how the application is performing.

The third stage involves gaining access to uncover the target’s vulnerabilities. Testers then exploit vulnerabilities by stealing data, increasing permissions, or intercepting traffic to assess the damage they can cause.

In the fourth stage, the tester attempts to maintain access to see if the vulnerability can be used long enough to gain in-depth access. It aims at determining whether the attacker can cause more harm.

The final stage involves covering tracks to remain undetected. The pen test results are compiled to reflect the specific vulnerabilities that were exploited, any sensitive data that was breached, and the amount of time the tester remained undetected in the system.


Pen Testing Tools

Pen testers usually use automated tools to detect standard application vulnerabilities. These tools scan code to uncover malicious code in applications that could result in a security breach. They also assess data encryption techniques to identify hard-coded values like passwords and usernames to verify security vulnerabilities. Features of penetration tools include:

● Simple configuration, deployment, and use
● System scanning
● Automated verification of vulnerabilities
● Detailed vulnerability reports and logs
● Ranked vulnerabilities based on their seriousness

Most pen testing tools are free and open source, which gives testers the ability to change or customize the code for their own needs. Some common free and open source pen testing tools include The Metasploit Project, Nmap, Wireshark, and John the Ripper.


Types of Penetration Testing

The type of penetration testing usually depends on the organization’s scope and specific requirements. There are three types of pen testing, including black box penetration testing, white box penetration testing, and gray box penetration system.

1. Black Box Penetration Testing

In this test, the tester has no idea about the systems being tested and collects information about the target network. The tester attempts to find a vulnerability to exploit. This type of test is costly and can take a long time to complete, and the tester usually depends on automated processes.

This test’s main advantage is that it simulates a real-world cyber-attack where a potential attacker is uninformed. It is also known as a trial and error approach and requires a high degree of technical skill.

2. White Box Penetration Testing

This a comprehensive test where the tester is provided with full knowledge and has access to the software architecture and the source code. The main objective is to conduct an in-depth security audit of the organization’s systems and gain as much information as possible. The test is more conclusive and takes up less time since the tester has more access to information.

One of the main disadvantages of this test is that the tester may take time to decide what to focus on precisely due to the level of access. It also requires complex and costly tools such as debuggers and code analyzers. It is also known as clear box or open box testing.

3. Gray Box Penetrating Testing

In this test, the tester is given partial information or access to the web application or internal network. Access is limited to gaining access to the software code and the system’s architecture diagrams. This test is usually non-intrusive and unbiased since the tester does not require access to source code.

This test’s main advantage is that the reporting offers a more efficient and focused assessment of the network’s security. Both automated and manual testing processes can be utilized in the test, and there is usually a higher chance of finding security vulnerabilities with this method.


Approaches to Penetration Testing

There are various penetration testing approaches, including network services, web application, client side, wireless, social engineering, and physical penetration testing.

Network Services

Network service penetration testing or infrastructure testing aims to identify the most exposed vulnerabilities and security weaknesses in the network infrastructures. These infrastructures include servers, routers, artificial intelligence, printers, operating systems, workstations, firewalls, and more.

A network service penetration test is usually performed to protect an organization from common network-based attacks. These attacks include:

● Firewall bypass and firewall misconfigurations
● Router attacks
● IPS/IDS attacks
● DNS level attacks
● SSH attacks
● Proxy server attacks
● Database attacks
● FTP/SMTP based attacks
● Unnecessary open ports attacks
● Proxy server attacks
● Man In The Middle attacks
● Identify IP address spoofing

A network offers mission-critical servers to an organization, and it is therefore advisable that both internal and external network penetration tests be undertaken at least once a year. This will boost your organization’s security against potential attackers.


Web Application Penetration Testing

This kind of testing is used to detect security weaknesses or vulnerabilities in web-based applications. The test uses different penetration techniques that target the web application. The extent of the test includes web-based applications browsers and their components.

These tests are considered more sophisticated since they are more detailed and targeted. They require ample time and effort to plan and successfully execute these tests to develop a meaningful report.

The main objective of performing a web application test is to detect security vulnerabilities within the web-based application and its components. It also helps to prioritize vulnerabilities and offer possible solutions to deal with them.


Client Side Penetration Testing

This test is used to detect security weaknesses or vulnerabilities in client-side applications. These could be applications or a program such as web browsers, Adobe Photoshop, and Macromedia flash.

These tests are performed to identify specific cyber-attacks such as:

● Cross-site scripting attacks
● Clickjacking attacks
● Cross-origin resource sharing (CORS)
● Form hijacking
● HTML injection
● Openredirection
● Malware infection


Wireless Penetration Testing

This test involves identifying and accessing the connections between all devices connected to the organization’s Wi-Fi. They include tablets, laptops, smartphones, and others. They are usually undertaken on site, and the tester needs to be in close range to access the wireless signal. A mobile NUC and Wi-Fi pineapple can also be used remotely for the test.

Wireless penetration tests are performed to secure the wireless network from any vulnerabilities like data leakage and unauthorized access. It is important to ensure that all access points are identified and how many lack strong encryption methods.


Social Engineering Penetration Testing

These tests are used to tick or persuade users into providing them with sensitive information like usernames and passwords. Common attacks include:

● Phishing attacks
● Vishing
● Smishing
● Tailgating
● Imposters
● Name Dropping
● Pre-texting
● Dumpster Diving
● Eavesdropping
● Gifts

These tests help prevent cyber-attacks based on internal users since they are one of the biggest threats to network security. They are also very lucrative and may tempt an internal user to give up sensitive information. They can be avoided by offering remediation training to inform and educate users on the most current cyber-attacks out there.


Physical Penetration Testing

In this method, a tester attempts to gain physical access to an organization’s infrastructure, systems, building, or employees by breaching physical barriers and the security team.

It exposes vulnerabilities and weaknesses in physical security controls like barriers, locks, sensors, or cameras. The organization can then put proper mitigations to strengthen physical security posture.

Contact us to learn more about penetration testing. We offer a customized approach that will be targeted to what your company needs.