A better way to conduct enterprise penetration testing

Penetration testing for enterprise security operationalizes the function of security testing for an organization's offensive security program.

Centralizing penetration testing into a core function of the enterprise can provide significant ROI; however, it also requires a new level of considerations, that when applied correctly, can significantly improve overall security outcomes.

The Demand for Pentesting within the Enterprise

Like any compliance-driven, point-in-time pentesting, enterprises are conducting penetration tests regularly to discover and address security issues before hackers exploit them. This proactive testing helps to meet their compliance requirements and launch projects on time.

When compared to how other organizations conduct pentesting, the key difference for the enterprise is the sheer demand these organizations must fulfill. Across the enterprise, there are multiple internal stakeholders who have pentesting requirements to fulfill. Beyond the CISO, central pentesting teams are delivering pentests for product owners, GRC (governance, risk, and compliance), DevSecOps, and more. In some of these central departments, hundreds and thousands of penetration tests are requested every year. This causes a pentesting backlog that can cause unintended security and compliance risks due to a lack of resources.

With that in mind, it’s important to understand the best methods to conduct penetration testing services for the enterprise require a unique, tailored approach. Compared to other organizations, enterprises face challenges that take time, resources, and trusted partners to help solve -- and not all penetration testing providers are the same.

The Enterprise Penetration Testing Approach

Within the enterprise, trained security staff can perform security tests in-house, or an outside security firm can conduct them. Organizations at the enterprise level may have in-house experts capable of conducting an offensive security test; however, in-house testing may not be as thorough or unbiased as a third-party tester.

Compliance requirements are also a consideration here; most requirements call for an independent, third-party penetration testing provider. However, conducting in-house assessments to complement the scheduled penetration testing is a strong method to strengthening security maturity.

Enterprise penetration testing includes a measured, planned out approach with a dedicated central team that manages bulk penetration testing. IT staff can perform tests in-house or an outside security firm can conduct them. Organizations at the enterprise level may have in-house experts capable of conducting an offensive security test; however, in-house testing may not be as thorough or unbiased as a third-party tester.

The Need for Full-Stack Penetration Testing

Depending upon their specific industry and government requirements, enterprises have multiple types of penetration tests that pentesters can perform. Cybersecurity-driven compliance regulations will impact each penetration test’s scope, focus, and goals.

The typical roster of full stack pentesting that enterprise organizations need to conduct regularly includes the following:

• An External Network Penetration Test simulates an attack on an organization’s external IT networks. In this test, penetration testers test external websites, web applications, servers, and network infrastructure exposed to the internet.

• An Internal Network Penetration Test simulates an attack on an organization’s internal IT systems and network. In this test, penetration testers conduct testing on the internal network infrastructure, servers, workstations, endpoints, and internal software applications.

• An API Penetration Test simulates an attack on an organization’s applied programmable interface (API). In this test, penetration testers assess and scan for security vulnerabilities that expose an organization’s sensitive data or provide a foothold for cyber criminals via the API, which can lead to a digital supply chain attack.

• A Web Application Penetration Test simulates an attack on an external web application and/or website. In this test, penetration testers hunt for critical vulnerabilities, like cross-site scripting (XSS), SQL injection, and remote code execution, with the objective of identifying the most critical web app vulnerabilities that have the highest likelihood of being exploited.

• A Mobile Application Penetration Test assesses the security of the organization’s mobile application. In this test, penetration testers scan for critical vulnerabilities, such a compliance issues or highly exploited known vulnerabilities, that can be discovered for remediation.

• A Cloud Penetration Test assesses an organization’s cloud computing infrastructure. In this test, penetration testers hunt for cloud vulnerabilities, misconfigurations, unmonitored virtual machines, and exposed sensitive data on public cloud assets.

Finally, social engineering testing and phishing simulations are also needed, yet the execution will be unique to each enterprise. These types of tests attempt to trick employees into revealing sensitive information or breaching security protocols. Each enterprise will take a different approach to meet their various industry and compliance requirements to test the efficacy of their security awareness training.

Ethical hackers may deploy several tactics in social engineering tests, including:

• Reconnaissance using OSINT tools and techniques, along with dark web scans to hack company-owned assets with breached user credentials;
• Simulated phishing emails, fake SMS texts, imposter phone calls, or deepfake videos to trick users into giving away access credentials; and,
• Physical tactics, such as leaving a malware-loaded USB stick in the company’s parking lot, to see if employees can be tricked in the real world by a threat actor.

4 Benefits to Enterprise Pen Testing as a Service

Penetration testing is tremendously useful for evaluating and improving enterprise IT security, but it comes with challenges that must be mitigated with new approaches to old problems.

With the new evolution of pentesting, called Pen Testing as a Service (PTaaS), enterprise directors and CISOs can explore testing that scales for the enterprise. PTaaS gives enterprises capabilities to enable central pentesting teams with significant capabilities to reduce security risks immediately while improving security outcomes over time.

Four benefits that can be immediately gained by any enterprise shifting to PTaaS include the following:

1) Faster Mitigation of Preventable Breaches

One of the most obvious benefits of routine penetration testing at the enterprise-level is that it reduces the probability of devastating cyberattacks and security breaches that lead to expensive financial and reputational damage. By performing penetration testing on the IT infrastructure of an enterprise, security teams can identify and remediate vulnerabilities and fix security weaknesses quickly, thereby increasing the difficulty of a cyber intruder successfully gaining a foothold inside your network.

2) Comprehensive Visibility to See What the Adversary Sees

The enterprise penetration test report delivers a macro view to ‘see’ exactly what areas are exposed attack surfaces that threat actors can see and scan for vulnerabilities. The enterprise pentest also delivers a point-in-time view of potential attack paths that could be used – categorized with tags to map to threat models, such as MITRE ATT&CK, and frameworks, such as the NIST CSF. Enterprise-level penetration testing combines offensive security expertise, threat intelligence, analytics, artificial intelligence, and human-validated artifacts to demonstrate how vulnerabilities could be exploiting along a kill chain in a real attack.

3) Capabilities to Meet Regulatory and Compliance requirements

Penetration testing is often conducted to comply with industry-specific laws and government regulations. For example, organizations that take payment card security must routinely perform external and internal penetration testing for PCI DSS standard for routinely; these requirements will increase when PCI DSS 4.0 is required in 2025. Rather than searching for specific compliance validation reports, enterprise penetration testing includes scanning for and identifying potential compliance gaps and issues in the IT environment within a scoped penetration test. This accelerates the ability for internal stakeholders to demonstrate compliance with a certified pentest report for auditors.

4) Supports Remediation with Integrated Guidance and Risk Scoring

Penetration testers produce reports on which security vulnerabilities exist in a company, how to fix them, and which ones are the most dangerous. With pen test findings in hand, the experts in the enterprise’s Security Operations Center and DevSecOps teams can triage vulnerabilities discovered during the penetration test and address the most critical ones first. These routine activities and integrated workflows help enterprises mitigate cyber risks using DevSecOps best practices for continuous vulnerability management.

Enterprise Penetration Testing at a Glance

Pen Testing as a Service combines the advantages of AI innovation, a proven methodology, and Human-led pentesting can now help the enterprise penetration testing program scale and eliminate the pentesting backlog. This enterprise-grade solution gives control back to the central penetration testing team and their internal stakeholders to streamline penetration testing while offering complete visibility to the enterprise’s CISO.

When considering PTaaS, it’s critical to evaluate potential providers to ensure you can gain the capabilities you need to succeed.

Download The CISO’s Guide to Enterprise Penetration Testing

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Megan Charrois is Marketing Executive at BreachLock Inc. BreachLock’s award-winning, analyst-recognized PTaaS solution helps customers do more with their cloud-native PTaaS portal and 12-months of vulnerability management benefits. The BreachLock Client Portal offers customers the ability to connect 24/7 for on-going vulnerability scanning and retesting benefits that continue for 12-months from the start date of the penetration test. For more information, schedule a discovery call with one of BreachLock’s security experts to see why PTaaS has become the new go-to for enterprise central penetration teams, and how it can work for you today.