The Ultimate Guide to Penetration Testing: Frameworks, Steps, and Checklists for Success

Cybersecurity strategies need to constantly evolve to keep up with the ever-changing threats. Penetration testing, often shortened to penetesting, has become a big part of safeguarding against those cybersecurity threats. Penetesting simulates a cyberattack on your system, network, or application to pinpoint weak points before hackers can exploit them.

While these tests can be incredibly helpful in identifying weaknesses and building your organization’s defenses, proper steps are necessary to ensure success. It’s important to lean on applicable frameworks, follow the correct steps, and check your boxes to ensure you complete a successful and effective penetest.

Importance of Penetration Testing Execution Standards (PTES)

Adhering to established standards is a must for effective penetration testing. The Penetration Testing Execution Standard (PTES) details a specific framework for testing procedures, helping promote consistency and quality across the board. It covers every step of a penetration test, from pre-engagement interactions to reporting, helping testers provide actionable insights to stakeholders.

While it’s often revered as the most comprehensive penetesting standard, it isn’t the only one. Other well-known standards that cover penetration testing include the NIST Cybersecurity Framework, which provides guidelines to manage and reduce cybersecurity risks, and the OWASP Testing Guide, which focuses on web application security and provides a detailed methodology for pinpointing vulnerabilities.

Whichever guideline you choose, following these standards can help your organization achieve more thorough and reliable risks, reducing the chances of overlooking risks.

Steps in the Penetration Testing Process

Penetesting is a multi-step process, with each step expanding on the findings or results of the previous phase. A well-executed penetration testing process should comprehensively uncover all potential weaknesses. Penetration testing steps include:

1. Planning and scoping: During this stage, you need to define clear objectives, scope, and goals of the test. Figure out what type of testing you plan to use, such as black-box, white-box, or gray-box. Get the permissions you need to proceed and establish a timeline.
2. Reconnaissance: In this phase, you’ll gather information about the target system using publicly available data. Stick to passive methods to avoid detection.
3. Scanning: Now, use automated tools to find vulnerabilities in the system. Complete both static and dynamic analyses to find possible entry points.
4. Exploitation: Attempt to exploit the vulnerabilities you found to determine their severity. In this process, demonstrate the actual impact of those weak points without causing real damage.
5. Post-exploitation: Look back on your findings and evaluate how far an attacker could potentially penetrate the system. Assess the potential fallout of an attack and gather information for remediation efforts.
6. Reporting: Document everything you found, including the vulnerabilities you exploited, providing detailed recommendations for fixing each one. Present the report in an easy-to-understand way, free of technical jargon that might confuse stakeholders with a non-technical background.

Overview of Penetration Testing Frameworks

When testing for vulnerabilities, it’s important to lean on established frameworks. This way, you can ensure your penetesting process is structured, efficient, and effective. Popular options include:

• OWASP Testing Guide: This focuses on web applications. It provides a methodology for pinpointing and reducing vulnerabilities, plus tools and techniques for testing application security.
• NIST Cybersecurity Framework: This takes a risk-based approach to managing cybersecurity, including guidelines for identifying, protecting, detecting, responding to, and recovering from threats.
• MITRE ATT&CK® Framework: This is a knowledge base full of adversarial tactics and techniques. It helps testers simulate real-world attack scenarios and carefully evaluate the effectiveness of current security controls.

Each penetest framework is a bit different, but all three offer structured methodologies to help your organization tailor testing to your specific needs and compliance requirements.

Building a Penetration Testing Checklist

Before you begin, create a detailed checklist. This way, you won’t accidentally miss any must-do steps during a penetest. Your penetest checklist should include:

• Pre-test prep, including a definition of the test’s scope and goals, obtaining necessary permissions, informing relevant stakeholders, prepping necessary tools, and confirming that testing environments are isolated.
• In-test actions, including gathering data on the target system through reconnaissance and scanning, actively testing for vulnerabilities via automated tools and manual techniques, and documenting every stage for transparency and reproducibility.
• Post-test activities, including compiling a detailed report that outlines your findings, their impact, and remediation steps, and conducting a debrief with stakeholders to discuss what you found and the necessary next steps.

Understanding Penetration Testing Requirements

Compliance is huge for industries across the board. Failure to comply with applicable standards can open the door to various headaches, including legal consequences and reputational damage, so it’s important to maintain compliance. This includes during penetrating testing.

When conducting your organization’s penetesting, be sure to comply with any applicable standards. These might include:

• PCI DSS (Payment Card Industry Data Security Standard): This standard requires regular penetration tests for organizations handling cardholder data.
• HIPAA (Health Information Portability and Accountability Act): This standard enforces security measures to protect sensitive health information.

Adjust and implement penetration testing as needed to meet regulatory requirements. Doing so can ensure your organization remains compliant while addressing industry-specific risks.

Best Practices for Successful Penetration Testing

Without the right steps, penetration testing may not be as effective as it could be. So, to maximize the effectiveness of your organization’s penetration testing, implement best practices:

• Collaborate with stakeholders: Include all relevant parties in testing, including IT teams, management, and third-party providers. This way, you can verify that your goals and expectations are aligned across the board.
• Choose the right tools and frameworks: Not all tools and frameworks are right for every organization. Choose options that match your organization’s needs and the test’s objectives. Generally, a blend of automated and manual testing yields the best results.
• Ensure ethical and legal compliance: Never start penetesting without proper authorization. Always get the permissions you need before beginning. Following ethical guidelines helps preserve trust and skirts unintended consequences.
• Conduct regular testing: Penetesting isn’t a one-and-done activity. Instead, regular testing is necessary to find vulnerabilities as they arise. With routine testing, you can ensure that you identify and mitigate any vulnerabilities in a timely manner.

Strengthen Your Cybersecurity Through Penetration Testing

Penetration testing is an indispensable element of a well-rounded cybersecurity strategy. It allows your organization to simulate real-world attacks, ensuring you can identify vulnerabilities and strengthen your defenses before hackers can exploit them. With structured penetesting, guided by standards like PTES, NIST, and OWASP, you can thoroughly and effectively protect your systems.

If you’re ready to take your cybersecurity strategy to the next level with managed IT services or need help with your organization’s penetesting, our team at Safepoint IT is here to help. We can help you uncover hidden vulnerabilities to protect your business from potential breaches. Contact us today to learn more about our security services.