A Guide to Pen Testing and Red Teaming: What to Know Now

Penetration testing and red teaming are essential cybersecurity practices that bolster an organization’s security posture by uncovering vulnerabilities within their systems, networks, and people or business processes. These methodologies have distinct objectives, scopes, approaches and technologies employed.

Despite the significance of both penetration testing and red teaming to bolster an organization’s cybersecurity program, organizations are often unfamiliar with the differences between the two. Penetration testing is a targeted simulated attack on a particular system or network, aiming to discover and report vulnerabilities susceptible to exploitation. This type of testing is designed to evaluate primary controls such as patch and vulnerability management, system configuration and hardening, encryption, application security, network segmentation, privileged access management and security policy enforcement. The scope of this engagement is defined, and the cost varies based on the extent and depth of the assessment.

Alternatively, red teaming offers a targeted evaluation of an organization’s security posture, often focusing on a threat actor’s ability to gain unintended access, along with testing detective and preventive controls.

• Detective controls include intrusion detection systems (IDS), endpoint detection and response (EDR), security information and event management (SIEM) systems, log analysis and anomaly detection.
• Preventive controls involve firewalls, access control lists, intrusion prevention systems (IPS), multi-factor authentication (MFA) and network segmentation.
• The objective is to identify and exploit vulnerabilities in a manner akin to an actual attacker, while also gauging the organization’s capacity to detect and prevent attacks.

Red teaming is an objective-based exercise aimed to simulate real-world threat actors targeting an organization. Such objectives typically include compromising the internal environment starting from an external perspective, sensitive system access, or business process disruption. Attack paths or attacker methodologies leveraged during red team exercises support in evaluating an organization’s resilience against various threat actors, including nation-states, organized crime, and insider threats. This approach necessitates highly skilled testers who must work slowly, deliberately and quietly to evade detection, which can result in a higher cost to execute compared to penetration testing. The complexity and sophistication of the exercise, the need for extensive research and reconnaissance and the requirement for a higher level of coordination among testers and the organization are some of the factors that contribute to the higher cost.

Either…or?

When choosing between penetration testing and red teaming, organizations should base their decision on their specific objectives and risk tolerance.

• For red teaming in particular, companies should tailor the scope and objectives to focus on areas of key risks.
• For example, a healthcare system might prioritize protecting medical records, an R&D organization could emphasize safeguarding intellectual property and organizations with large or complex procurement processes might concentrate on securing financial data.
• By aligning the testing methodology with these critical risk areas, organizations can effectively address potential vulnerabilities and their impact on the organization’s reputation, compliance and financial well-being.

In terms of technology, both practices employ various tools and techniques such as automated vulnerability scanners, manual penetration testing utilities and bespoke scripts to assess the target networks and systems.

• Red teaming aims to simulate real-world threat actors.
• All tools and techniques are typically considered within scope but may not necessarily be used.
• Red teaming may also incorporate social engineering tactics and physical security assessments to evaluate employee security awareness and adherence to security policies.

Vital cybersecurity practices

Penetration testing and red teaming are vital cybersecurity practices that aid organizations in pinpointing and addressing potential vulnerabilities in their systems, networks and business/people processes.

• Engaging external, unbiased experts for these assessments can offer fresh perspectives and uncover issues that internal teams may overlook.
• It is crucial to not only identify vulnerabilities but also to prioritize timely remediation and validation to strengthen the organization’s overall security posture.
• By considering findings that are developed as part of a red team or penetration test, senior leaders can make informed decisions on how to effectively protect their organization’s assets and maintain a strong security posture.

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