Estimated read time 7 min read
Estimated read time 7 min read

In cybersecurity, the term ‘pentesting‘ is no stranger to professionals. Nevertheless, despite its familiarity, it often carries a certain level of obscurity. Thus, it is essential for us to dissect this concept and gain a comprehensive understanding of what pentesting truly encompasses.

The Nitty-Gritty of Pentesting: What Does it Mean?

Pentesting, or penetration testing to give it its full name, is a proactive cybersecurity strategy. It involves the authorized, ethical hacking of a system, network, or application with the primary goal of uncovering any underlying vulnerabilities. In the simplest terms, pentesting plays the role of a digital health check-up, identifying the potential loopholes in your cyber armor that might attract unwanted guests.

Benefits of Pentesting

Moving beyond the what to the why, let’s discuss the tangible benefits that pentesting brings to the table:

Tailored Incident Response Plans

Every cybersecurity infrastructure is unique, with its own set of challenges and risks. Pentesting helps in developing customized incident response plans that suit the specific needs of an organization. By identifying potential threats and vulnerabilities, pentesting ensures you’re not just reacting to threats, but proactively preparing for them.

Swift Response Times

Incidents are inevitable, but with the insights gained from penetration testing, the response can be swift and efficient. The understanding of your unique vulnerabilities allows the response team, whether on-site or remote, to target their efforts effectively and control crises quickly.

Comprehensive Report and Future Recommendations

Perhaps the most valuable output of pentesting is the detailed report it generates. This document, rich with information, not only lists out the vulnerabilities and incidents but also provides recommendations for the future. It’s like a roadmap that guides your security measures, keeping them aligned with your unique needs and potential threats.

Constant Protection

While threat management services are your first line of defense, pairing them with pentesting results in a robust 24×7 protection system. It’s not just about fighting threats; it’s about hunting them down before they can cause any harm, all under the watchful eyes of certified cybersecurity professionals.

Pentesting and GDPR

GDPR (General Data Protection Regulation) has made secure data processing a priority for all businesses. Pentesting is instrumental in ensuring this security. It checks whether the technical and organizational measures in place to secure personal data processing are effective, thus aiding in GDPR compliance.

Pentesting: Methodologies and Standards

With the basics of pentesting out of the way, let’s delve a bit deeper and explore some of the widely accepted penetration testing methodologies and standards. These frameworks ensure that the pentesting process is comprehensive, reliable, and consistent, covering all essential aspects of a system’s security.

Pentest Stages
Pentest Stages

Open Source Security Testing Methodology Manual (OSSTMM)

The OSSTMM is a methodology that provides a comprehensive, scientific framework for the security testing of various systems, from web applications to internal networks. It emphasizes the understanding of how operational security works and how data and human interactions affect this. The OSSTMM’s primary goal is to quantify the operational security in a system, not just list vulnerabilities.

Open Web Application Security Project (OWASP)

OWASP is an open-source project dedicated to web application security. It’s best known for the OWASP Top Ten, a powerful awareness document that lists the most critical security risks to web applications. OWASP also offers testing guides that provide a framework for identifying and mitigating web application vulnerabilities.

National Institute of Standards and Technology (NIST)

NIST’s penetration testing guidelines, part of its broader cybersecurity framework, provides a solid foundation for conducting pentests. NIST’s approach is thorough and risk-focused, emphasizing regular testing, clear communication, and the integration of pentesting into a larger risk management framework.

Penetration Testing Execution Standard (PTES)

The PTES aims to offer a standard practice that can be used by both the security community and the business sector. It covers everything from the pre-engagement interactions and intelligence gathering to threat modeling, vulnerability analysis, and the reporting of the findings.

Information Systems Security Assessment Framework (ISSAF)

The ISSAF is a free and open methodology for conducting security assessments. It provides comprehensive guidance for each phase of the pentesting process and includes extensive checklists to ensure that no stone is left unturned.

Pentesting: Methodologies and Standards
Pentesting: Methodologies and Standards

Automated Vs. Manual Pentesting

Understanding Automated Pentesting

Automated pentesting involves the use of software tools to scan and probe systems for vulnerabilities. These tools can quickly and efficiently check for thousands of known vulnerabilities, misconfigurations, and other potential security issues.

The significant advantage of automated pentesting is its speed and scalability. It can scan large networks and systems in a fraction of the time it would take a human tester. It’s particularly good at finding well-known, common vulnerabilities that are often overlooked due to their simplicity.

However, automated tools have their limitations. They can generate false positives, and they often lack the ability to find complex vulnerabilities that require a sophisticated understanding of the system’s context. Additionally, they’re not as adept at identifying issues with business logic, an area where manual pentesting shines.

Delving into Manual Pentesting

Manual pentesting, on the other hand, involves a cybersecurity professional personally conducting the testing. Using their knowledge and skills, they probe the system, seeking out vulnerabilities that automated tools might miss.

Manual testers can also understand the unique context and usage of the system, helping them find vulnerabilities that are specific to the system’s architecture or its use within the organization.

The strength of manual pentesting lies in its depth and flexibility. A human tester can adapt and evolve their testing approach as they learn more about the system, making their testing more thorough and nuanced.

However, manual pentesting can be time-consuming and resource-intensive, and it may not be practical for large systems or networks.

Combining Both for Optimal Results

In practice, the most effective pentesting often involves a combination of both automated and manual methods. Automated testing tools can quickly identify the low-hanging fruit – common vulnerabilities and misconfigurations – allowing the pentesters to focus their manual testing efforts on the areas where they can provide the most value.

A combined approach offers the best of both worlds, using the efficiency and breadth of automated testing to complement the depth and adaptability of manual testing.

Optimal Frequency of Penetration Testing

A commonly raised query relates to the ideal frequency for penetration tests. Traditional practices often recommend annual assessments, or tests linked to significant infrastructural or application changes. However, the evolution of software development methodologies has necessitated a shift in this approach.

In an era where Agile, DevOps, and CI/CD models drive continuous, incremental updates to applications, it’s clear that the frequency of testing must adapt in stride. Regular, even constant, security checks become imperative to maintain a robust security posture amidst rapid changes.

One method to tackle this challenge is through Continuous Scanning services. This strategy kicks off with manual tests on the applications, followed by automated tests carried out monthly, weekly, or bi-weekly, depending on the specific requirements.

Given the frequency of these tests, the resulting reports primarily highlight deltas, or differences, from the previous report, ensuring a focused update on new findings or changes.

Go even deeper

Great to see that you are interested in learning more. Well, don’t stop, continue with the following Pentesting resources:

  • Regularly Assessed Domains in Pentesting (Link)