Types of Penetration Testing: Choosing the Best One for Your Company

Organization security is an ever-changing consideration. A company may achieve an optimal level of protection at one point in time, but after a server reconfiguration or the installation of new network devices, it may soon become completely vulnerable again. Over time, failures also occur in systems that were considered reliable. For this reason, companies periodically conduct different types of attack simulations to significantly reduce the risks associated with a changing environment. 

Basically, penetration testing, or pen testing in short form, is a method of simulating a cyber attack by security professionals in order to find and take advantage of vulnerabilities in a computer system, network, or application. 

Performing penetration tests has numerous benefits, after all, it:

• Helps determine the degree of vulnerability of information systems, as necessary for taking corrective measures.
• Identifies security flaws after configuration changes.
• Identifies systems at risk due to obsolescence.
• Identifies misconfigurations that could lead to safety failures of network devices (switches, routers, firewalls, etc.), etc.

In our article, we will look at the main penetration testing variations, features and their applications, in order to help organizations choose the most appropriate kind of pentest according to their needs.

Different Approaches to Penetration Testing

Black-box: no insider information available

The name basically gives away what this kind of penetration testing is all about. The black-box is one of the penetration testings in which absolutely nothing is known in advance. The pentester must therefore gather all the necessary information independently and search for it in the systems themselves. He can then work with this pool of various information in the further course of the test, but is not provided with any additional information. This is an important point in this scenario of penetration test, which is virtually essential.

White-box: full knowledge of the system

The white box is a kind of pen testing in which the pentester, i.e. the ethical hacker, has full access to the program code, the documentation and all details of the IT entities used. “Attackers” therefore know in advance exactly which kind of IT system and IT infrastructure he is attacking and what they need to pay special attention to, as they already have knowledge that a normal hacker would never have in advance.

Gray-box: partial system visibility

Defined as a mixture of the two previous kinds of penetration assessments, the gray-box: or “gray-box” already has some specific information to perform the evaluation. Understanding the possible attacks is crucial, as it allows focusing on specific attacks that could leverage known liabilities.

However, this amount of information is low and does not compare to the amount of data available in a white-box.

3 Classifications of Penetration Testing Types

These classifications are based on the testing scope and the environment in which vulnerabilities are assessed. Each approach targets distinct vulnerabilities, providing a comprehensive view of an organization’s security posture.

1. External and Internal Penetration Tests

A penetration test may be performed externally or internally to simulate diverse attack vectors. This classification is based on the perspective from which the test is conducted and the potential threat sources being evaluated.

• External penetration assessment: Focus on assessing the safety of a business social-facing entities and infrastructure, such as websites, web applications, and internet-accessible servers. This variation of pentest evaluates the organization's defenses from the perspective of an external attacker.
• Internal penetration testings: On the other hand, identify the protection of an organization's internal systems and networks, simulating the actions of attackers who have already gained access to the network.

2. Local and Web-Based Penetration Testings

A penetration test can also be classified, based on the environment and entities under evaluation, into being either local or web-based. This assists a business in finding particular vulnerabilities related to both local and online operations.

• Local pen assessments: Involve pentesting the security of entities and applications that are installed and running on the user's local machine or within a local network. This includes assessing the security of desktop applications, operating systems, and any other software or services running on the local entities, ensuring that they are protected against attacks.
• Web-based penetration assessments: In contrast, focus on evaluating the safety of web-based applications, websites, and web services that are accessible over the internet. This type of pen testing examines what vulnerabilities and security weaknesses that could be exploited by an attacker through the web interface.

3. Types of Penetration Testing by Focus Area

Penetration testing variations vary depending on the type of entities or environment, methods and approaches, and the level of knowledge of the tester. Let’s overview them and summarize the main aspects. 

Network Penetration Test

Network penetration testing is one of the most common kinds of penetration testing. Testing is conducted to find out an organization's most vulnerable points in network infrastructure, such as servers, firewalls, switches, routers, printers, and workstations.

The great number of penetration testers tries to implement some tactics used by the old pirates, such as wrapping malicious traffic in false flags so that the traffic appears to be just regular network activity or sending out distress signals to fake out entities into allowing unauthorized access. That would presuppose attempting to avoid security controls and trying to infiltrate the network using some techniques and attacks, meaning methods unseen by anyone. 

Web Application Test

Web application testing is more complicated for the tester compared to other forms of penetration testing, as web applications are dynamic in nature, and the code can be flexibly deployed. Researchers in security have found that many companies still use very outdated versions of popular web application frameworks and content management entities that are vulnerable to known exploits.

Penetration testers find vulnerabilities related to improper input validation, broken access controls, and security misconfigurations on a regular basis that allow them to access things that they should not have been able to. In addition, this complexity requires substantial knowledge from an attacker both in the architecture of the application itself and the possible attack vectors.

Wireless Penetration Test

The rise of software-defined radios (SDRs) has allowed penetration testing teams to more effectively emulate various kinds of wireless devices during security assessments. This enables them to conduct more comprehensive evaluations of wireless network exposures.

Cloud Penetration Test

Cloud penetration testing evaluates the security of cloud environments and can be structured around:

• IaaS (Infrastructure as a Service): Focuses on the security of virtual machines, networks, and storage configurations.
• PaaS (Platform as a Service): Assesses the security of application development platforms, including database configurations.
• SaaS (Software as a Service): Targets the security of software applications, emphasizing user access controls and data protection.

During cloud environment test, common pitfalls are often found related to improper system configurations, inadequate privileged account management, and insecure data storage practices. These issues can expose cloud-hosted resources and data to potential compromise.

Mobile Application Penetration Test

Automated tools are becoming increasingly prevalent in mobile application security pen testing, as they can efficiently detect exposures related to encryption issues and improper handling of user data. These tools help pen testers identify mobile-specific security weaknesses more effectively.

Social Engineering Pen Test

One of the common tactics used by social engineers is the use of manipulative techniques that mislead and aim to obtain confidential information from employees. This approach relies on human psychology rather than technical breaches.

IoT Penetration Test

During Internet of Things security testing, pitfalls are often found related to outdated software, inadequate device protection, and weak default passwords across connected devices. These issues can leave IoT entities exposed to potential compromise.

IoT testing includes three subtypes:

• Device testing: Evaluates the security of individual IoT devices for vulnerabilities like outdated software.
• Communication channel testing: Assesses the security of data transmission between devices, focusing on protocols and encryption.
• Mobile application testing: Examines the security of mobile apps interacting with IoT devices, identifying data handling and access control vulnerabilities.

API Penetration Test

Security experts have discovered that many companies do not pay enough attention to thorough this testing, leading to the emergence of critical exposures that can be exploited through attacks. Ensuring comprehensive security assessment is crucial to mitigate these groups of risks.

Insider Threat Penetration Test

During internal penetration assessments, exposures are often found related to improper management of employee access privileges and lack of proper monitoring of their actions. These issues can enable malicious insiders to gain unauthorized access and cause harm to the organization.

Container Penetration Test

The containerization technologies have dramatically changed the approach on how applications are deployed and scaled today, with Docker and Kubernetes leading the charge. In an effort to make sure that these container-based environments are secure, pen testing has now evolved to evaluate the security of these environments, so organizations can isolate and mitigate risks that would otherwise leave their containerized applications and infrastructure wide open to threats from attacks.

CI/CD Penetration Test

CI/CD pipelines have opened a wide range of attack vectors for pen testers. That's where security tester comes in: tester makes security test a CI/CD toolchain, which involves version control, build automation, and deployment platforms, searching for vulnerabilities that would allow an attacker to compromise the sensitive resources in the process. 

Conclusion

With the constantly changing digital landscape, selecting the type of penetration testing is key to protecting your organization's assets. Every test variation offers different information and brings into focus different vulnerabilities, helping you build specific safety strategies. Investment in the right approach towards penetration testing is one surefire way to ensure a resilient future for your business, especially in the face of growing attacks.

We look forward to helping you secure your digital environment against attacks. 

Reach out to Datami today!