In the dynamic and ever-evolving landscape of cyber security defenses, enterprise-grade penetration testing is one of the most crucial practices for organizations to adopt. 

With cyber criminals operating on a far more sophisticated level than ever, continuous and multi-layered security testing, across internal and external infrastructure, is key for enhanced resilience.

However, organizations may find that with such a broad spectrum of expanding threats and technologies, a targeted penetration testing service may be more suitable than others. 

This guide seeks to uncover those points of differentiation, how each type works and why and when they should be performed.

Understanding the different classifications of penetration testing is vital for security analysts to determine the best solution for their organization’s unique requirements.

Exploring The Dynamic Penetration Testing Space

In simple terms, penetration testing (pentesting as the vernacular) refers to exercises and strategies that exploit vulnerabilities and weaknesses in internal/external systems, 5G networks, or assets.

The main quirk of penetration testing solutions is that all exercises are cautiously performed to assess security controls and their effectiveness.

In other words, they act completely ethically despite the possibility that their actions may resemble or be similar to those of a cybercriminal or malicious entity.

Tests may involve using sophisticated social engineering techniques, phishing emails to access critical databases, accounts, and systems, or shared passwords to access sensitive data.

Deploying Email Managed Detection and Response is an essential part of the hardening of the system to prevent the intrusion of all types of attacks, including advanced phishing, BEC, etc.

Some attack methods may be visible and intrusive, while others may be covert and innocuous, bearing some similarities to red and purple team exercises that often take place without the organization’s security or IT staff’s prior knowledge. 

This methodology sounds fairly simple, but not all penetration testing exercises follow the same formula.

There are numerous types of pentesting, including tests on network services, web applications, and physical media that are available for firms to enlist.

What Do Tests Need?

Tests may be performed internally or externally to simulate and validate different attack vectors, with some penetration testing experts – usually outsourced professionals from an approved and verified cyber security provider – having complete, moderate or even zero knowledge of the incumbent environment or systems they are attempting to hack ethically. As such, tests may be deemed anything from black box to white box exercises.

“Scoping plays an essential role in any penetration testing engagement” says Mark Nicholls, Chief Research Officer of the CREST-approved penetration testing company, Kroll. “Our accredited security experts work with our customers to develop a testing program that aligns with the unique requirements of each organization.

Our experts enable businesses in a range of industries to uncover and address complex vulnerabilities across their internal and external infrastructure, whether that includes wireless networks, cloud services, web apps, mobile apps, APIs or network builds and configurations.“

While the end goals of penetration testing services may remain the same (i.e. evaluating specific aspects of an organization’s multi-layered security posture), it’s fair to say that not all tests are created equal. 

“The main goals of any penetration test are tied to our clients’ overarching business strategies,” Nicholls continues. “Many of our clients are regulated by third-party statutory bodies that mandate specific forms of security testing, while others need to build testing programs to support mergers and acquisitions, new application releases or other significant infrastructure changes.

Pentesting Examples

Businesses sector-wide may be facing more red tape and regulatory pressure to deploy specific compliant solutions and robust software that aligns with particular security frameworks. 

An application-specific penetration test can identify flaws and weaknesses in ‌native and server-side code that could expose the vendor and users to attacks.

Analysts then provide a report to the client’s appointed representative (usually a senior business leader) to provide direction and guidance for developers to follow that fixes errors while reducing risk exposure. 

Penetration testing reports can vary drastically, depending on the complexity and setup of a business’s infrastructure, its objectives, the tools, software and endpoints being tested, the perceived value of the assets, and so much more.

So it’s clear that penetration testing differs in approach, strategy, and execution from organization to organization. Broadly speaking, however, it’s important to decipher the sub-types of testing exercises.

Penetration Testing Types

Network penetration testing

Network service testing (or infrastructure testing) focuses on evaluating the security of an organization’s internal and external networks. 

This type of testing aims to identify vulnerabilities that could be exploited in the network infrastructure, such as firewalls, routers, switches, PCs, and other devices connected to a network.

Common network-based attacks include MITM (man in the middle), DNS, IPS/IDS, proxy server, FTP/SMTP and open port attacks, to name just a few.

Tests can be simulated from outside network perimeters or internally as if a perpetrator has already gained a foothold within the network and has moved laterally across the infrastructure.

Social Engineering Penetration Testing

Social engineering attacks target the human element of an organization’s security posture. In an ethical scenario, ‘malicious actors’ attempt to persuade and deceive users into divulging sensitive information, login credentials, and administrator access to critical systems. 

Social engineering pentesting techniques include phishing emails, vishing (voice phishing), tailgating, name-dropping, eavesdropping, and disguising oneself as a known entity or individual on the pretext of legitimacy.

Social engineering tests employee awareness, response time and tactics, and attitudes towards security.

Application Penetration Testing

Application penetration testing evaluates the security of web applications, desktop applications, and browsers and their components such as ActiveX and Silverlight. These complex tests evaluate the endpoints of every web-based application that interacts with – or is used by – the user. 

Software application development relies heavily on defined CI (continuous integration) and CD (continuous delivery) pipelines, in that developers regularly try to enhance and improve codebases.

Agile code deployment is preferred over batch methods, as sandbox environments (i.e. duplicate codebases) can be used to test functionality and usability before live deployment.

Penetration testing would exploit this architecture as part of its continuous code testing.

Client-side Penetration Testing

Client-side penetration testing evaluates the security of client-side components, such as web browsers, browser extensions, and client-side scripts. 

This type of testing aims to identify vulnerabilities that could be exploited through cross-site scripting (XSS), clickjacking, HTML injections, open redirection, malware infections and other client-side cyber attacks.

Wireless Penetration Testing

Wireless networks usually are the single resource that provides network connectivity to various internet of things (IoT) devices in an on-site environment, such as laptops, tablets, smartphones, servers, drives, and so on.

The right wireless pentesting involves identifying and examining the connection security of these devices and the siloed network.

Wireless penetration tests will usually require the complete identification of access points, invalid encryption methods (e.g. HTTPS), monitoring systems in place, misconfigurations, network duplicates, access point protocols (e.g. WPA3) and authentication mechanisms.

Any vulnerable access or unencrypted connection point can be divulged with the help of pentesting.

Physical Penetration Testing

Physical penetration testing assesses the physical security controls and measures in place to protect an organization’s facilities, data centers, and other critical infrastructure.

Physical barriers are often overlooked as far as cyber security is concerned. Still, if a criminal were to gain physical access to servers, drives, and assets, then they could knowingly exploit all connected data.

This testing involves ‌ethical attempts to gain physical access to restricted areas, bypassing security controls, and evaluating the effectiveness of physical security measures such as access control systems, surveillance cameras, and employee awareness.

Black Box, White Box, And Gray Box Penetration Testing

Penetration tests can also be classified based on the level of information provided to the testing team:

1.Black box (external) penetration testing: In this type of testing, the testing team has no prior knowledge of the target environment, mimicking the scenario of an uninformed and opportunistic external attacker.

2.White box (internal) penetration testing: In white box testing, the testing team has full knowledge and access to the target environment, including source code, system configurations, and networks, simulating an insider threat scenario. 

3.Gray box penetration testing: Gray box testing falls between black box and white box testing. The testing team has partial knowledge of or access to the infrastructure or application, reflecting a scenario where an attacker has gained some information about the target.

The right pentesting approach can provide valuable insights and direction to help organizations strengthen their security posture and navigate the complex threat landscape with increased confidence and peace of mind.