How do you define the scope and goals of a pen test project?

When defining the scope of a pen test, it's important to align it with business objectives and risk factors. During a recent project, I was asked to conduct a gray-box pen test for a financial services firm. Given the sensitive nature of their customer data, we scoped the test to include critical assets such as their payment processing systems and customer databases. By limiting the scope to these high-value targets, we were able to focus our efforts on what posed the greatest risk to the business. This allowed us to deliver more actionable insights within a limited timeframe and budget. It's crucial to engage with stakeholders early to ensure the scope covers key risk areas without overextending the project’s resources.

Before proceeding, it is crucial to define why the customer needs the test. Whether evaluating compliance with specific standards such as PCI DSS or ISO 27001, prioritizing remediation efforts based on risk exposure, validating security controls and policies, or simulating real-world attack scenarios to test the effectiveness of response capabilities incidents, each objective guides the choices of appropriate methodology, tools and metrics.

I've been scoping out pen tests for about five years now, and I always try to find out why the client wants a pen test as a precursor to the scoping call. From there, I can recommend either something like a Red Team or Purple Team or, in my experience, scenario-based testing, which is usually the most appropriate for mature networks. Understanding why is one piece, understanding if they've had a pen test before because clients may say they want a "red team." However, this won't be as valuable if they've never had a pen test. I can plan out the pen testers, time, and costs with the type of testing derived.

Understanding the purpose of a penetration test is vital for setting clear objectives and achieving desired outcomes. Whether for compliance, risk assessment, control validation, or incident response simulation, defining goals guides methodology, tool selection, and metrics. With five years of experience, I prioritize understanding client motivations to recommend tailored testing approaches like Red Team or scenario-based testing, aligning with network maturity. Assessing past tests informs optimal resource allocation for maximum effectiveness.

To effectively conduct a pen test, first define its purpose: Are you aiming for compliance, assessing risk, validating security controls, or simulating real-world attacks? Your goals will determine the methodology, tools, and metrics used in the test.

Setting clear goals for a pen test ensures that the results align with your organization's security strategy. In one engagement with a healthcare provider, the goal was not just to find vulnerabilities but to assess how quickly the IT team could detect and respond to threats. We simulated an attack on their patient data management system, focusing on testing their incident response capabilities. This red team-blue team exercise revealed gaps in their monitoring processes, which we documented and used to improve their response times. By tailoring the goals to test both technical weaknesses and human factors, we helped the client enhance their overall security posture.

The choice between a vulnerability assessment to identify weaknesses and a full exploration to exploit them presented unique challenges and opportunities. Furthermore, the decision to focus on a specific pen test, whether for networking, web, wireless or mobile, highlighted that each option addresses different crucial aspects of the security infrastructure. But it is essential that the customer knows what they are purchasing and that an evaluation is different from a pen test, so understanding the customer's needs is important.

Defining a penetration test's scope involves choosing between black-box, white-box, or gray-box tests to determine the level of tester information access. Specifying target systems, networks, and applications is crucial. Deciding on vulnerability assessments or full exploitation determines testing depth. Selecting network, web, wireless, or mobile pen tests focuses on different infrastructure aspects. The scope dictates duration, cost, and complexity. Employing time boxing offers flexibility, while considering travel for wireless pen testing is essential to plan effectively.

How many web application do you want to test ? How many static and dynamic pages in this website ? How many user roles in this website? These are some samples of questions to define the scope and create approximate sizing

One thing I've found responding to proposals for the past few years is that you cannot always ask clients for quantities, like #of IPs, # of Web Apps, etc. Many don't know or what it to be black-box and you have to find out. Alternatively, you can scope an engagement by time boxing -- for example, 1 week to test your public facing web app and maybe 3 days for public facing assets (external pen test). My time boxing instead of dealing with counts, you have greater flexibility if you only find 10 IPs but the scope was 100 (where'd the other 90 go). It's crucial to understand if wireless pen testing is required as that may also require travel.

The reporting phase is just as important as the testing itself, as it determines how effectively the findings are acted upon. In a recent pen test for an e-commerce company, we uncovered several critical vulnerabilities in their web application. We didn’t just stop at reporting the issues; we worked closely with their development team to walk through the report and explain how to remediate each vulnerability. By presenting the results in a way that was accessible to both technical and non-technical stakeholders, we ensured that the recommended fixes were implemented quickly and effectively, reducing the risk of future exploitation. This collaborative approach makes the report more impactful and actionable.

Pentester set the goals follow below stepes 1.Identify Critical Vulnerabilities: Uncover key system weaknesses like SQL injection or XSS. 2.Assess Impact and Likelihood: Evaluate the risk and potential impact of successful attacks. 3. Test Security Defenses: Measure the effectiveness of firewalls, IDS, and antivirus solutions. 4. Enhance Security Awareness: Conduct red team-blue team exercises to boost security skills. 5. Ensure Compliance: Meet regulatory requirements by identifying security gaps. 6.Improve Security Posture: Provide recommendations to enhance overall security and reduce breach risks.

Setting goals to measure the impact and likelihood of successful attacks, such as data theft or DoS, provided valuable insight into our organization's security posture. Furthermore, the intention to test the effectiveness of security defenses, including firewalls and antivirus, highlights specific areas for the organization to invest in and need to increase its resilience.

In setting penetration test goals, prioritize pinpointing critical vulnerabilities like SQL injection. Assess the impact of successful attacks such as data theft and gauge the effectiveness of defenses like firewalls and antivirus. Enhance security skills through red team-blue team exercises. These objectives serve as benchmarks for measuring the test's success and value. Analyzing successful attack impacts provides insights into security posture, while testing defenses identifies areas for improvement and investment to bolster resilience.

Set clear goals for your pen test by defining specific objectives, such as identifying critical vulnerabilities, measuring potential attack impact, testing defense effectiveness, or enhancing security skills. These goals will help evaluate the success and value of the pen test.

Defining a clear time and ways for the client to follow up becomes a differentiator, mainly so they can be sure that the tests are happening and that they will be delivered in a timely manner without any delay and the entire scope will be covered, no matter what type of test it is.

The most important document a pen test team needs is a Rules of Engagement to outline what can and cannot be done during the testing. Like out-of-scope IP addresses and URLs, POCs if something goes wrong, times of day testing can occur, tools that are allowed or not allowed, types of attacks or personnel that are out of bounds, and more. Most pen test teams should have this templated and approved so you can efficiently work with your client.

Establishing rules for a pen test involves defining engagement boundaries such as timing, frequency, and duration, along with communication channels and escalation procedures. Specify allowed methods, techniques, and tools, and document these rules in a contract or statement of work to address legal and ethical concerns.

Having a specialized team is essential, for this it is important to invest in employees to be prepared and carry out tests in different scenarios, be it a consultant or an information security professional. The more skills the team has and the more experience, the better the test will be, especially a prepared team that understands business logic and has good technical skills.

To choose the team for a pen test, decide between in-house staff or a third-party provider. Consider factors like expertise, budget, and availability. Evaluate candidates based on credentials, reputation, references, and adherence to industry standards.

When I chose my pen test team, I considered several factors. I start with client expectations. Some clients require specific certifications, and based on that requirement, I will 'filter' out my pool of resources. Then, I consider the type of testing. Some of my testers are good at social engineering, some are good at Web Apps, and others are best at network testing. Once I know who to use, I confirm their availability and modify where needed. For me, budget is last. I would instead give a quality pen test report to the suitable testers!

Testing is significant, but the real value of pen testing is reporting your findings to your clients. As part of the understanding and scoping sections, you should understand what regulatory frameworks drive the discussion. So, I always include a mapping to the regulator framework of the client's choice. - Additionally, each finding should include: 'steps to reproduce' ensuring all the necessary steps are identified with screenshots - CVSS score - CVE if applicable (many pen test findings don't have CVEs yet) - MITRE ATT&CK mapping - Risk valuation (High, Moderate, Low) - Impacted URL or Host(s) - Recommendations for remediation - Test IDs, if applicable - Executive summary - Other items agreed to by your team or the client

Delivering penetration test results involves thoroughly analyzing findings and recommendations. The report must encompass scope, goals, methodology, metrics, vulnerabilities, exploits, impacts, and remediations. Reviewing the report with the tester and discussing next steps is pivotal. Including regulatory framework mappings, detailed findings with reproducible steps, CVSS scores, CVEs (if applicable), MITRE ATT&CK mapping, risk valuation, impacted URLs or hosts, remediation recommendations, test IDs (if applicable), an executive summary, and agreed-upon items ensures a comprehensive and actionable report for enhancing security posture.

A critical vulnerability like SQL injection is found in the organization's web app. Despite firewalls and antivirus, attackers exploit it, leading to a data breach. This underscores the need to test security measures rigorously. It stresses ongoing improvement and investment in defenses to mitigate risks effectively and fend off potential threats.