What is penetration testing in cybersecurity?

Penetration testing, also known as pen testing, is a proactive approach to cybersecurity that involves authorized attempts to breach an organization's computer systems, networks, and applications to evaluate their security posture and identify vulnerabilities before they can be exploited by attackers.

The process of ethical hacking imitates real-world attacks using the same tools and techniques as a malicious actor. Penetration testing provides a vital check on the strength of an organization's defenses, reduces the risks posed by cyber threats, and ensures compliance with industry standards and regulations.

Types of penetration testing

The approach to penetration testing can be classified into three categories: black box, white box, and gray box testing. In black box testing, the penetration tester has no prior knowledge of the environment or systems being assessed, mimicking how an external attacker with no internal information would operate. White box testing, on the other hand, grants the tester complete access and knowledge about the environment. Gray box testing falls in between, where the tester has partial knowledge or limited access.

Network penetration testing

This form of penetration testing concentrates on discovering vulnerabilities within an organization's network infrastructure. The primary goal is to uncover weaknesses like misconfigured firewalls, open ports, or outdated network protocols, which could potentially grant unauthorized access to attackers.
Web application penetration testing

Web application pentesting identifies vulnerabilities specific to web-based applications. It aims to uncover various weaknesses such as SQL injection, cross-site scripting, and insecure authentication mechanisms that could allow attackers to steal sensitive data or gain control over the targeted application.
Wireless network penetration testing

This type of testing focuses on testing the security of wireless networks and identifying vulnerabilities that could be exploited. The goal is to identify weaknesses such as weak encryption, rogue access points, or unsecured Wi-Fi networks that could allow attackers to intercept sensitive information or launch a man-in-the-middle attack.
Mobile application penetration testing

The focus of mobile application penetration testing is to identify vulnerabilities within mobile applications that could potentially be exploited by threat actors. It seeks to uncover vulnerabilities such as insecure data storage, weak authentication mechanisms, and insecure network communications. Exploiting these vulnerabilities could enable attackers to seize control of the mobile device or steal sensitive data.

The penetration testing process

usually involves the following five steps:

01. Reconnaissance

The initial stage of penetration testing, known as reconnaissance, forms the foundation of the entire process. During this phase, the pen tester undertakes an intelligence-gathering mission to gather information about the target system. This includes details like IP addresses, domain information, network services, mail servers, and network topology.
02. Scanning

During this phase, a thorough technical examination of the target system takes place. Tools such as port scanners, vulnerability scanning software and network mappers are employed to gain information about the target systems.

Scanning allows testers to assess the behavior of the target application in different scenarios and pinpoint potential vulnerabilities that could be exploited.
03. Exploitation and vulnerability verification

In this phase, the penetration testers may attempt to exploit the vulnerable areas located within the scope of the penetration test. This phase also allows the penetration tester and the organization to verify the severity of weaknesses identified within the systems.
04. Maintaining access and privilege escalation

Once the pen testers have access to the target environment, they maintain access and escalate privileges, attempting to move laterally through the system and access sensitive data and systems.
05. Reporting and documentation

At the final stage, the penetration testers compile their observations, findings, and remediation steps into a report for the target organization. The report includes pertinent recommendations for the organization to enhance its security measures.

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Red teaming vs penetration testing

While both red teaming and penetration testing involve using ethical hackers to identify security vulnerabilities, they differ in terms of scope, objectives, approach, and depth. Here are some of the differences between red teaming and penetration testing:

Scope and approach

Penetration testing typically focuses on identifying vulnerabilities in a specific system, application, or network. It follows a systematic approach aiming to uncover vulnerabilities and provide recommendations for remediation.

On the other hand, red teaming takes a broader and more holistic approach by simulating real-world attacks. It involves an organized team working to simulate a simulated attack campaign with predefined objectives, which may involve multiple systems, applications, and even physical security measures.
Objectives

In penetration testing, the goal is to find and exploit as many vulnerabilities as possible to assess security weaknesses. The focus is on uncovering technical vulnerabilities and providing recommendations for improving security.

In contrast, red teaming aims to simulate realistic and targeted attacks to identify weaknesses in an organization's overall security posture. It assesses people, processes, and technologies to provide a more comprehensive evaluation of an organization's ability to detect and respond to advanced threats.
Approach to testing

Penetration testing typically follows a predefined methodology, involving specific tools and techniques to uncover vulnerabilities and assess their impact.

Red teaming, on the other hand, takes a more adversarial approach, aiming to replicate an attacker's perspective. It involves creative thinking, reconnaissance, and social engineering techniques to bypass defenses and simulate real-world attack scenarios.
Engagement duration and depth

Penetration testing engagements tend to be relatively shorter in duration and focused on a specific target. The testing is often conducted within a predefined time frame, with a set of specific objectives.

Red teaming engagements, on the other hand, are typically longer in duration and involve a more comprehensive assessment of an organization's security.

What are the goals of penetration testing?

Identifying security weaknesses

By scanning for potential vulnerabilities in an organization's computer systems, networks, and applications, the organization can take corrective action to prevent cyber attacks.
Staying ahead of cyber threats

Cyber threats are constantly evolving, but pen testing is constantly looking for vulnerabilities. As those threats change, penetration testing makes the organization aware, in nearly real-time, of new threats.
Assessing potential impact

The impact of a data breach can be significant, and it's essential to assess the potential impact of a breach on the organization. Pen testing helps identify high-risk areas, providing an assessment of vulnerabilities before an attacker can take advantage of them.
Compliance and regulations

Many organizations are subject to regulatory compliance regimes, including PCI-DSS, HIPAA, and GDPR. Penetration testing helps organizations meet these regulatory requirements and ensure that sensitive customer data is protected.
Building a strong cybersecurity culture

Penetration testing helps build a strong cybersecurity culture within an organization by demonstrating the risks and potential consequences of cyber attacks. As employees gain an understanding of these risks, they become more invested in maintaining security best practices.

Importance of penetration testing training

Penetration testing training is critical for pentesting teams as it enhances their technical skills and knowledge, keeps them updated with evolving threats, establishes effective testing methodologies, ensures compliance with regulations, and improves communication and reporting capabilities. By investing in training, organizations can build highly skilled pentesting teams that can effectively evaluate and strengthen their security posture.

Benefits of penetration testing

Comprehensive security assessment

Penetration testing provides a comprehensive assessment of an organization's security posture and helps identify vulnerabilities that may go undetected by other testing methods.
Identifying security vulnerabilities

Penetration testing helps identify areas of an organization's systems and applications that may be vulnerable to attack. This allows the organization to prioritize and address high-priority vulnerabilities, leading to a more secure environment.
Validation of security controls efficacy

Penetration testing validates the effectiveness of an organization's security controls in protecting against a real-world attack.
Protection of customers and shareholders

By identifying vulnerabilities and taking steps to remediate them, organizations are better able to protect their customers' and stakeholders' sensitive information.
Avoidance of brand damage

A data breach can significantly damage an organization's brand reputation and trust. By conducting penetration testing, organizations can identify and remediate vulnerabilities before they can be exploited by threat actors, mitigating the risk of a data breach and associated brand damage.
Regulatory compliance

Penetration testing helps organizations meet regulatory compliance regimes like PCI-DSS, HIPAA, and GDPR to ensure that sensitive customer data is protected.

Gateway to expert-level penetration testing: OffSec's penetration testing training solutions

OffSec is a globally recognized and trusted provider of industry-leading training and certification programs for penetration testing teams. Organizations worldwide turn to OffSec to enhance the skills and capabilities of their teams in the following ways:

Unmatched penetration testing training:

OffSec's suite of penetration testing courses equips cybersecurity professionals with comprehensive skills, catering to various platforms and complexities.

PEN: Network Penetration Testing Essentials

This is a fundamental-level Learning Path designed to prepare learners to begin their penetration testing journey. This learning path covers the main concepts of information security such as cryptography, scripting, networking protocols, and working with shells.
PEN-200: Penetration Testing with Kali Linux

The PEN-200 course with OffSec Certified Professional (OSCP) certification provides practical, real-world training that equips teams with the skills and knowledge needed to conduct thorough and effective assessments.
PEN-210: Foundational Wireless Network Attacks

This course introduces learners to the skills needed to audit and secure wireless devices and is a foundational course alongside PEN-200 and benefits those who would like to gain more skills in network security.
PEN-300: Advanced Evasion Techniques and Breaching Defenses

The PEN-300 course with OffSec Experienced Pentester (OSEP) certification teaches learners to perform advanced penetration tests against mature organizations with an established security function and focuses on bypassing security mechanisms that are designed to block attacks.

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SEC-100: CyberCore - Security Essentials

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Additional resources

Ongoing professional development

OffSec's training programs are not limited to initial certification. They offer foundational to advanced courses and continuous learning opportunities to support the ongoing professional development of penetration testing teams. This enables organizations to provide their teams with the resources and support they need to stay at the forefront of the penetration testing field. Through OffSec's training programs, organizations can establish a culture of continuous learning and improvement within their teams.
Global community and support

By participating in OffSec's training programs, organizations gain access to a global community of like-minded professionals. This community provides valuable networking opportunities, knowledge sharing, and support channels. Organizations can leverage this community to exchange ideas, collaborate on challenging problems, and stay connected with the latest trends and best practices in the penetration testing domain.