The 11-Step Pen Test Plan

In today’s interconnected world, technology has become an integral part of our lives, shaping various aspects of society. However, this increased connectivity has also brought about significant changes in the threat landscape. Cybercrime and cyber insecurity have emerged as formidable adversaries, earning their place among the most severe global risks for the next decade, as highlighted by the World Economic Forum. With cybercrime now holding the 8th spot among the most severe global risks along with climate change and involuntary migration, it is clear that no organization can afford to be complacent.

Penetration testing, also known as ethical hacking, is a vital tool in this battle. By simulating real-world attacks, pen test exposes weaknesses in computer systems, networks, and applications, empowering security teams to fortify their defenses effectively. Yet as every security professional knows, conducting a successful penetration test is no easy feat. A well-executed test requires complex decision-making, planning, a budget, and internal expertise.

A meticulously crafted pen test plan ensures that all requirements are clearly defined, roles are assigned, and security and compliance goals are outlined well before the engagement commences. Its significance lies not only in facilitating a smoother testing process but also in safeguarding against security breaches. By leveraging a comprehensive plan, organizations can proactively identify vulnerabilities and fortify their defenses, ensuring that their digital fortresses remain impervious to attacks.

In this blog post, we’ll cover the essentials of the ideal pen test plan that aligns with security compliance standards such as PCI DSS, HIPAA, etc. By defining objectives, scoping the engagement, assembling a skilled team, conducting reconnaissance, and identifying vulnerabilities, you can proactively identify security weaknesses. Additionally, documenting findings, implementing remediation strategies, and scheduling regular assessments help address these weaknesses effectively.

Why is a pen test plan needed?

Conducting a successful penetration test is no small feat. It requires intricate decision-making, meticulous planning, allocated budgets, and internal expertise. Given the prevalent understaffed security teams and budget constraints faced by organizations today, these investments are even more crucial and must be thoughtfully planned. By dedicating time and effort to building a well-designed pen test plan, organizations can navigate these challenges and ensure a success engagement.

A carefully crafted pen test plan serves as a roadmap for conducting a thorough, compliant, and secure assessment. It outlines the objectives, scope, and methodologies to be employed during the testing process. The plan’s documentation includes a well-defined scope that specifies the particular system(s) to be tested, ensuring that all relevant aspects of the IT infrastructure are examined. Depending on the type of test being conducted, the plan encompasses essential details such as known assets, users, and regulated data that need to be systematically examined.

It’s worth noting that even in a black box penetration test, where a third party is not provided with technical information beforehand, there will still be a plan in place to conduct the test effectively. This plan includes timing details, assigned personnel, remediation assignments, and other essential considerations.

Who will conduct the Pen Test?

One of the key challenges in managing breach risks during a pentest is identifying individuals with the necessary specialized expertise to carry out the test. This responsibility can be assigned to either an in-house ethical hacker or a certified external expert from a qualified third-party provider. Regardless of who conducts the pentest, it is crucial to have a well-defined plan with a clear scope to ensure success.

When conducting a penetration test in complex hybrid environments, traditional pen testing methods may prove inadequate. To tackle this challenge, modern security operation centers can benefit from AI-enabled pen test providers like BreachLock. With Pentesting as a Service (PTaaS), CISOs can extend their in-house resources with human expertise enabled with AI and automation capabilities. The advantages of such an approach will yield faster turnaround time, cost optimization, and increased return on investment (ROI).

Creating Your Pen Test Plan in 11 Steps

Preparing for a penetration test can alleviate concerns about potential network outages or disruptions to your business systems and critical operations. As time is valuable, it’s important to minimize any inconveniences or operational bottlenecks during the testing process.
Use the following 11 steps as a structured approach to help plan your next penetration test for success.
1) Define Objectives and Scope

Scoping involves determining the systems, networks, or applications that will be tested, as well as any limitations or restrictions. Before initiating a pen test engagement, it is essential to establish clear objectives and define the scope of the assessment. Objectives will guide the testing process and ensure that the goals align with your organization’s security needs. Common objectives may include assessing the security of specific applications, identifying vulnerabilities in network infrastructure, or testing the effectiveness of security controls.

It is crucial to communicate the scope to the pen test team, ensuring that they have a comprehensive understanding of the target environment. This helps avoid any unintended disruptions or impacts on production systems during the testing process.

2) Assemble the Testing Team

Building a skilled and experienced pen test team is crucial for the success of your assessment. Look for professionals who hold relevant certifications such as Certified Ethical Hacker (CEH), Offensive Security Certified Professional (OSCP), or Certified Information Systems Security Professional (CISSP). Their expertise should cover a wide range of technologies, including network infrastructure, web applications, mobile applications, and wireless networks.

Additionally, ensure that the team members have a solid understanding of the latest hacking techniques, tools, and methodologies. Consider engaging external pen test firms with proven track records to bring in fresh perspectives and expertise.

3) Choose a Testing Methodology

Select an appropriate testing methodology based on your objectives and requirements. Common methodologies include black box, white box, or gray box testing. Black box testing simulates an external attacker with no prior knowledge of the system, while white box testing involves deep knowledge of the system’s internal workings. Gray box testing falls somewhere in between. Choose the methodology that aligns best with your security and compliance goals.

In addition to selecting a testing methodology, it is essential to consider the specific techniques that will be employed during the assessment. Some common pen test techniques include social engineering, API pen test, application security testing, etc.

4) Design the Test

When designing the test plan for pen test, it is essential to create a detailed outline that includes specific testing activities, techniques, and tools to be utilized. The design of the test should include the steps that will be followed in the test, along with the allocated times for each activity. In this phase, it’s crucial to consider any prerequisites that may hinder the test’s design, such as access credentials or testing agreements, to ensure a smooth and efficient testing process.

When selecting a security testing framework like OWASP or the NIST CSF, consider the specific nature of the systems, applications, or networks under examination. Evaluate the relevance and applicability of the framework’s guidelines to your environment. Taking into account industry standards, regulatory requirements, and specific security concerns will aid in choosing the most suitable framework.

Read more on how to select the right security framework for your next penetration test: What Cybersecurity Framework Works Best for Pen Test?

5) Obtain Authorization

Obtaining authorization from relevant stakeholders is a critical step in the pen test process. This involves seeking written permission to ensure legal and ethical compliance, prevent misunderstandings, and mitigate potential disruptions during testing.

When conducting penetration tests on cloud applications or security technologies, it is essential to consider the requirements and stipulations set by the service provider. Providers like Amazon Web Services have clear terms and conditions regarding when conducting an AWS pen test, and it is important to review and follow them.

In some cases, additional authorization may be necessary when working with third-party providers or cloud services like endpoint detection or firewall testing. This involves seeking permission from the relevant service providers and complying with their terms of service and shared responsibility models. Following these guidelines ensures that the engagement remains within legal boundaries and maintains a safe and compliant environment.

6) Conduct Reconnaissance

The reconnaissance phase involves gathering information about the target systems, networks, or applications that will be tested. This phase involves the use of both passive and active information-gathering techniques. Additionally, OSINT tools (open source intelligence) can be utilized to aid in the reconnaissance process. Passive techniques involve searching publicly available information, such as corporate websites, social media profiles, job postings, and dark web intelligence to gain insights into the organization’s infrastructure. Active techniques, on the other hand, involve network scanning and enumeration to identify potential entry points.

The goal of reconnaissance is to build a comprehensive profile of the target environment, including IP ranges, system architecture, software versions, and potential vulnerabilities. This information serves as a foundation for the subsequent phases of the pen test plan.

Once the scoping, authorizations, and reconnaissance have been completed, it is time for the pen test exercise to formally begin.

7) Perform an initial Vulnerability Assessment

Conduct a vulnerability assessment to identify potential vulnerabilities within the target systems and applications. This can involve using automated tools, manual testing techniques, and examining configuration settings to identify weaknesses. The vulnerability assessment is used as a baseline to document the known vulnerabilities within the system being tested.

8) Execute the Pen Test

After defining the objectives, scope, and test plan, it is time to execute the penetration test. During this phase, a combination of manual testing techniques, vulnerability exploitation, and simulated attack scenarios are used to identify vulnerabilities and assess the effectiveness of security controls.

By executing the penetration test in line with the defined objectives, scope, and test plan, organizations can identify vulnerabilities, assess their impact, and make informed decisions to strengthen their security posture and improve compliance readiness. Partnering with a modern pen test provider like BreachLock can further optimize the process and deliver enhanced results to augment the in-house team’s capabilities. With BreachLock’s proprietary methods that provide early remediation guidance, the in-house team can focus on remediating critical vulnerabilities in the asset inventory before the pen test is finalized to reach compliance and security outcomes faster and more affordably than with legacy providers.

For more information on how to select a modern pen test service provider, read The CISO’s Guide to Pen Test as a Service.

9) Document and Analyze Findings

As part of the pen test process, it is crucial to thoroughly document and analyze the findings. This involves documenting all identified vulnerabilities, their impact, and the potential risks associated with them. Additionally, classifying the findings based on severity and likelihood of exploitation is important for prioritizing remediation efforts effectively and quickly.

When documenting the vulnerabilities, provide detailed information about each one, including the affected systems, networks, or applications, as well as a clear description of the vulnerability itself. Document the potential impact the vulnerability could have on the organization, such as data breaches, system compromises, or service disruptions.

10) Report and Remediate

Prepare a comprehensive report that includes an executive summary, detailed findings, and recommendations for remediation. The report should provide clear guidance on prioritizing vulnerabilities based on their severity and offer actionable steps to mitigate the identified risks. Collaborate closely with stakeholders, including system administrators, developers, and management, to ensure that the identified vulnerabilities are properly understood and addressed. Monitor the progress of remediation efforts and maintain effective communication to ensure accountability and timely resolution.

11) Retest and Validate

After remediation, conduct a retest to verify that the identified vulnerabilities have been successfully addressed. This step is crucial to validate the effectiveness of the remediation actions taken and ensure that no new issues have arisen during the process. By retesting and validating the systems, networks, or applications. Continuous monitoring and retesting are essential to maintain a proactive and robust security posture in the face of evolving threats.

By following these steps, organizations can effectively plan and execute a penetration test, enabling them to identify and address security vulnerabilities, enhance their security posture, and protect their critical assets.

Plan for Success with Pen Testing as a Service

To maintain a robust security posture, pen testing should not be a one-time activity. Rather, routine testing and regular assessments help DevSecOps teams adapt to evolving threats and vulnerabilities in the digital landscape. One go-to to accelerate the process is working with a trusted pen test services provider. This allows organizations to continuously conduct pentesting as a service with third party security experts without incurring additional staffing or technology costs.

Creating a pen test plan is an essential way to mitigate critical risks and identify security vulnerabilities. These plans are particularly important when conducting additional risk and vulnerability assessments after significant changes, such as system upgrades, cloud migrations, or the release of new software, applications, or digital services. This proactive approach helps identify any new vulnerabilities that may have been introduced during these changes.

As a proven leader in delivering world-class, analyst-recognized Penetration testing as a Service, BreachLock has the expertise and resources necessary to secure your organization’s digital assets. Our certified experts provide the highest level of security validation, ensuring your organization remains protected against evolving threats. Our customer success and in-house security teams can start your next pen test within one business day. Our goal is to help clients accelerate meeting their security and compliance goals on time, every time.

Schedule a discovery call with one of our certified pen testing experts to plan your next pen test.