What Are the Different Types of Penetration Testing?

Penetration testing has one goal – to emulate the tactics that cyber criminals use to attack an organization’s systems. It’s a necessary component of any robust cybersecurity practice. However, it’s also a very broad term that actually encompasses a raft of different types of penetration testing. Each type of penetration testing serves a specific purpose as part of a holistic approach to cybersecurity.

There may be times when a full suite of penetration testing is needed. However, depending on the circumstances, you may only need a particular set of tests. For example, if you’ve just implemented a new cloud-based application, you may want to limit your testing to cloud and web security.

By understanding the different types of penetration testing, you can make an informed decision about which is the right one for your organization at any given time, based on your needs. Let’s dig in:

• Understanding the Types of Penetration Testing

• Black-Box vs. White-Box Testing

• Network Penetration Testing

• Web Application Testing

• Wireless Penetration Testing

• Cloud Penetration Testing

• Social Engineering Testing

• Types of Penetration Testing – Final Thoughts

You can consider penetration testing on multiple levels. The first level involves how easy it would be for a malicious party to breach your network from the outside or within.

The next penetration testing level goes more in-depth and examines the components of your organization’s system architecture. It discovers how an attacker could breach a web application, hack into a database stored in the cloud, or break into a secure WiFi network, for instance.

Finally, we have the human element. Employees are responsible for maintaining account security, keeping passwords and private keys secure, and generally implementing robust cybersecurity practices. Therefore, any comprehensive approach to penetration testing involves finding social vulnerabilities to cyberattacks.

Black-box or white-box testing refers to the amount of information the tester receives before running penetration tests. The types of penetration testing undertaken may be the same in either circumstance.

However, in black-box testing, the tester approaches your organization with no knowledge of its systems, as would an external attacker. In white-box testing, they perform the tests equipped with an understanding of the system architecture, including information such as integration connectors and entry points.

Network penetration testing is the most common of all pen tests. There are two types of network penetration testing – internal and external.

External Network Penetration Testing

External penetration testing aims to find vulnerable entry points to an organization’s network or applications that someone external to the organization could exploit. It assumes the attacker has no legitimate system credentials. Therefore, the starting point is typically organizational assets such as websites, email accounts, WiFi networks, or firewalls that are already facing out to the public. A tester will attempt to penetrate the perimeter of the network using these access points to get inside.

External penetration testing is useful for finding out if you’re inadvertently revealing any login information such as passwords or private keys that should remain confidential.

Internal Network Penetration Testing

Conversely, internal penetration testing assumes that someone has already managed to get inside your network or any given application. It could be an attacker who’s passed the external boundary, or an employee with some legitimate level of access.

Internal penetration testing aims to assess how far an attacker could move through your network. During the test, the tester may either use the entry point identified during an external test or a testing box set up for the exercise within the system.

From this position, the tester launches reconnaissance tools in an attempt to find weaknesses and vulnerabilities within internal systems. Often, the tester will take an escalating approach, targeting systems of lower importance and using data found in them to gain access to business-critical systems.

API and web application testing goes deeper than network penetration testing. This type of pen testing looks at each application that your organization uses and examines entry points, user permissions, APIs, and data hosted by third-parties.

The tester then launches a set of tools, such as web app scanners or proxy servers, aimed at exposing vulnerabilities. These tools attempt to uncover flaws in the application, such as data exposure, broken authentication and access controls, or security misconfiguration.

Integration has been a significant focus for many organizations on the road to digital transformation. However, having systems that are integrated through APIs and connectors like MySQL potentially introduces more points of weakness. Therefore, thorough web application penetration testing is necessary to ensure the end-to-end system architecture is secure.

Wireless testing is a type of penetration testing that analyzes the security of wireless devices and networks. These devices may include laptops, smartphones, and tablets but also internet of things (IoT) accessories, which may inadvertently provide a back-door into your wireless network.

A wireless pen tester looks at the overall WiFi network, including factors such as wireless encryption protocols, network traffic, password security quality, and unauthorized access points.

Many organizations now rely on third-party providers for cloud-based services, whether it’s software or infrastructure such as data storage. However, outsourcing these services means there’s a dependency on the provider to maintain sufficient security over whichever system or data they’re providing.

Pen testing cloud-based services involve simulating an attack through brute-forcing passwords or looking for weaknesses in APIs. It also checks the permissions for different roles assigned to users. These checks ensure that everyone has the appropriate access levels, and nobody can see data they shouldn’t have access to.

Cloud penetration testing will always be a collaborative effort between your organization and your provider. However, most public cloud providers have a policy that governs what can and cannot be done during cloud penetration testing. The policy will generally state whether or not you need to involve admins on your provider’s side.

Even with the most robust technical penetration testing, efforts can come undone if you neglect the human element. Malicious actors will often attempt to gain access to systems – or even physically infiltrate company premises – by manipulating employees into believing they’re legitimate.

Phishing is one such tactic. However, there are other ways that attackers can gain access to confidential information. Something seemingly innocuous like an organization chart or calendar could provide valuable information for name-dropping. All employees should be aware of the risks and back-doors into company systems. Education will help them to establish steps to safeguard all data and company property, such as access cards, cellphones, and laptops.

Penetration testing is one of the most valuable defenses against cyberattacks. Knowing which types of penetration testing can be used in which circumstances helps you improve your organization’s overall cybersecurity. Choose the right one and get protected today.