Getting Started with Penetration Testing

What is Penetration Testing

Penetration testing is a common procedure and an important element of an effective cybersecurity program. A penetration test, or “pen test,” is a simulated cyberattack conducted by ethical hackers to identify and exploit vulnerabilities in a system or network. The primary goal of a pen test is to assess the effectiveness of existing security measures and discover potential weaknesses that could be exploited. Penetration tests often involve a comprehensive evaluation of both technical and human factors, providing organizations with insights into how well their defenses hold up against real-world threats.

If your organization is getting started with penetration testing, here are some key elements to be aware of to get the most value and knowledge out of the procedure.

Why Penetration Testing is Important and Valuable

For your organization to comply with security and privacy standards like HIPAA, PCI DSS, and FISMA, it must conduct regular penetration testing. But cybersecurity is about more than complying with regulations or obtaining a security certification. Protecting your sensitive data and your customer’s data is a critical responsibility. A data breach can cost millions of dollars in fines, lawsuits, and recovery efforts. The damage to your reputation can negatively impact your business for years.

Pen testing is an effective way to put your cybersecurity program to the test, see how well it will hold up during an attack, and identify deficiencies and vulnerabilities that attackers could exploit.

Vulnerability Assessments and Penetration Tests are Not the Same

Pen tests and vulnerability assessments are complementary cybersecurity practices, but there are distinct differences between the two. A vulnerability assessment is an automated scan of external or internal networks for vulnerabilities. These scans utilize a database of signatures that have been crafted using known proof-of-concepts (PoCs). Pen tests are done manually by the tester. The vulnerability assessment can identify weaknesses, but unlike a pen test, does not try to exploit them. The vulnerability assessment provides much less information on the likelihood and potential impact of a cyber-attack than a pen test.

Pen testing can be used to target specific data that is of the highest concern to an organization and see if it can be exploited. A vulnerability assessment will provide a more general overview of network security and where patches or remediation may be needed.  However, vulnerability assessments cannot highlight misconfigurations within systems and networks, this is where a penetration test can become more specialized in its targeted focus.

Test All Vulnerable Areas

An attacker likely has multiple potential entry points to access your organization’s sensitive data. It’s important to test all areas that could expose your organization to risk. The following types of pen tests are available, and organizations should consider all that are applicable.

  • Network Testing – This can be done on internal or external networks. Testers will attempt to access the network by finding vulnerabilities in infrastructure such as routers, firewalls, switches, and more.
  • Web and Mobile App Testing – Finds vulnerabilities in apps by testing databases, source code, and backend networks.
  • Wireless Testing – Replicates entry attempts through Wi-Fi connections and wireless infrastructure.
  • Social Engineering – Ethically executes phishing and other social engineering campaigns to identify vulnerable individuals or groups within the organization.
  • Platform testing – Testers enter the servers (i.e. Windows, Linux, etc.) to penetrate any exposed services like authentication, file transfer, and file shares.

Find the Right Tester

You want the person conducting the pen testing to be qualified and experienced. Ask the vendors you are vetting what certifications their testers hold. Some highly regarded certifications in the industry include:

  • eLearnSecurity Certified Professional Penetration Tester (eCPPT)
  • HacktheBox Certified Penetration Tester (CPT)
  • GIAC Penetration Tester (GPEN)
  • Offensive Security Certified Professional (OSCP)

Define the Scope and Rules of Engagement

Work with your testing service provider to develop a project scope that meets your needs and addresses your organization’s goals for the test. Communicate to the testers what systems, networks, and applications will be included in the test. The provider will request information about your testing environment, IP addresses, URLs, etc., be sure to give them the most accurate and current information available.

Rules of engagement (ROE) set guidelines and boundaries for penetration testers during their assessment of the system or network. These rules are crucial for ensuring that the testing process is conducted in a controlled and ethical manner.

Use the ROE to specify what actions are allowed during the pen test and set boundaries for the tester. Some constraints often laid out in an ROE include:

  • Time windows for testing
  • Areas of the organization that can’t be disrupted
  • Systems or information that are off-limits for testing

 Communication protocols can also be established in the ROE.


When the testing is finished you should get a comprehensive report detailing the process, findings, and remediation strategies. Tell your service provider you want the following information in your report:

  • A description of the tools, techniques, and procedures employed during the test
  • An explanation of how the testing team approached the assessment
  • Detailed documentation of all vulnerabilities discovered, categorized by severity
  • Information on how each vulnerability was exploited
  • Evidence, such as screenshots or logs, to support the findings
  • Evaluation of the potential impact and likelihood of exploitation for each vulnerability
  • Specific, actionable steps to remediate identified vulnerabilities
  • Prioritization of recommendations based on risk severity

To dive deeper into penetration testing, listen to part 1 and part 2 of our The Essentials of Penetration Testing podcast.

CompliancePoint has a team of experienced cybersecurity professionals who can work with you to create a customized plan when you’re getting started with penetration testing or revamping your current strategy. Contact us at to learn more about how we can help.

Finding a credible expert with the appropriate background, expertise, and credentials can be difficult. CompliancePoint is here to help.