What is a Pen Test?
A penetration test (pen test) is a controlled cybersecurity assessment where ethical hackers attempt to breach your systems. The goal is to identify vulnerabilities before malicious actors can exploit them.
Penetration testing is often confused with vulnerability scanning. Over time, as scanning tools have advanced, some companies have misleadingly marketed vulnerability scans as “pen tests” to offer a cheap alternative. However, make no mistake—a vulnerability scan, while valuable within a vulnerability management program, is not the same as a full penetration test.
A proper pen test goes far beyond scanning and involves multiple phases, including:
- Scoping – Defining the goals, rules, and targets for the test.
- Reconnaissance – Gathering intelligence about the target.
- Scanning – Identifying weaknesses in the system.
- Exploitation & Lateral Movement – Actively attempting to breach security and move within the network.
- Post-exploitation – Assessing the potential impact of an attack.
- Reporting – Documenting findings with actionable recommendations.
While penetration testers may use vulnerability scanners as part of the reconnaissance or scanning phase, a true pen test involves human expertise, critical thinking, adaptive techniques, real-world attack simulation, and deeper security evaluations. When done correctly, a penetration test can reveal critical gaps in your cybersecurity program, including weaknesses in your vulnerability management processes and other security controls.
Why Should I Have a Pen Test?
Every week, another company makes headlines for falling victim to ransomware, financial fraud, or data breaches. How does this keep happening? Even organizations with established cybersecurity programs aren’t immune—no security system is perfect.
A penetration test is a proactive way to uncover vulnerabilities before attackers exploit them. If your business has never conducted a penetration test, you likely have unknown security gaps. A well-executed pen test provides real-world evidence of risks, turning hypothetical threats into actionable insights that help you strengthen your defenses.
A pen test can also assist with prioritizing remediation and initiatives, meeting regulatory requirements, validating your existing controls, and making better budget decisions.
Who Needs a Pen Test?
If you answer yes to any of these questions, your business could benefit from a penetration test:
- Do you rely on the internet for business operations?
- Do you store, process, or transmit sensitive data?
- Are you subject to regulatory requirements like PCI-DSS, HIPAA, or SOC 2?
- Do you accept or process digital payments?
- Do you communicate with customers or vendors via email?
If any of these apply to your organization, a penetration test can help identify weaknesses before cybercriminals do.
Types of Penetration Tests
Penetration tests come in different forms depending on the depth of access, attack vector, and business risk involved. The most common types include:
- Black Box Testing – The tester has no prior knowledge of the system.
- White Box Testing – The tester has full access to system architecture.
- Gray Box Testing – The tester has limited knowledge or user-level access.
- External vs. Internal Testing – External tests simulate attacks from outsiders, while internal tests evaluate insider threats and lateral movement.
- Web Application & Network Testing – Focuses on securing web apps, APIs, and network infrastructure.
- Social Engineering – Attempts to trick employees into revealing credentials or granting access.
- Physical Penetration Testing – Tests physical security measures, such as gaining unauthorized access to a facility or server room.
How Often Should You Have a Pen Test?
The frequency of penetration testing depends on your business size, risk profile, and compliance requirements.
- Regulated industries (PCI-DSS, HIPAA, SOC 2, etc.) often require annual penetration tests.
- Major infrastructure changes (new applications, cloud migrations, or network upgrades) warrant a test before deployment.
- Organizations with complex environments may stagger tests throughout the year, focusing on different areas, such as internal systems, web applications, and social engineering risks.
What Do I Need to Get a Pen Test?
To get started, follow these steps:
- Research and select a reputable penetration testing firm. Ensure they have qualified professionals and can provide references.
- Define a scope. If this is your first pen test, start with an external assessment before expanding to internal and application tests.
- Ensure leadership buy-in. Make sure your leadership team understands the goals, timing, and scope of the test.
- Get multiple quotes. Different firms have different methodologies, expertise, and pricing. Even two reputable firms can produce different but valid findings, as pen testing is both a science and an art.
- Rotate testers periodically. Mature cybersecurity programs switch penetration testers annually or every few years to ensure fresh perspectives and more comprehensive security assessments.
Ready to Get Started?
Protect your business before cybercriminals strike. Schedule your next penetration test today with Pinpoint Security and gain the insights you need to secure your organization.