What Do I Need and How Do I Prepare For a Pen Test?

So, you’re thinking about getting a penetration test – what do you need to do to prepare?

Penetration testing (pen testing) is a very important component of a comprehensive cybersecurity strategy. Before signing with a pen testing company, clients need to prepare effectively to maximize the benefits of the service. This paper outlines what clients should do, what they need, and how to prepare for a successful penetration test.

Understand the Purpose of Penetration Testing

Before beginning penetration testing, clients must understand the objectives. Penetration testing simulates real-world attacks to identify vulnerabilities in an organization’s systems, applications, and networks. The goal is to strengthen the overall security by addressing weaknesses. Clients should do the following actions below:

• Define the scope and goals of their penetration test.

• Determine if the test will focus on external, internal, web application, wireless, mobile testing, or social engineering vulnerabilities.

• Align penetration testing with compliance requirements like PCI DSS, HIPAA, or GDPR, if applicable.

• Set expectations for reporting and follow-up testing.

Assemble Internal Resources

Successful penetration testing requires collaboration and strong communication between the client and the cybersecurity company. Clients must inform their internal stakeholders so they are prepared for the process. Clients should do the following actions below:

• Assign a point of contact to coordinate with the penetration testing team.

• Notify relevant departments such as IT, legal, and management about the test if necessary.

• Make sure your employees are aware of the test to prevent confusion or disruption.

Prepare Technical Documentation and Access

Testers need technical information to perform their assessment. Your company must provide documentation and appropriate access. This will minimize delays and ensure accurate results. Clients should provide documentation below:

• Network diagrams, system architecture, and application details

• A list of IP addresses, domains, and systems within the test scope

• Access credentials (administrator accounts) if it is an internal test

• Details of third-party services or applications that may be part of the infrastructure

• Security policies and previous vulnerability assessments, if available.

Define the Scope Clearly

A well-defined scope ensures that the penetration test remains focused and effective. If you do not do this step, it can lead to wasted resources or missed vulnerabilities. You should do the following actions below:

• Exclude critical systems that cannot tolerate disruptions unless absolutely necessary.

• Determine the type of test you would like: black-box (no prior knowledge), gray-box (limited knowledge), or white-box (full knowledge).

Address Legal and Compliance Considerations

Penetration testing involves simulated attacks, which may have legal and compliance implications. Clients must ensure that the testing process follows all relevant regulations:

• Obtain proper authorization for the pen test.

• Make sure that the cybersecurity company has insurance coverage.

• Make sure that contracts include confidentiality agreements to protect sensitive data.

• Communicate with other parties if external vendors or cloud services are within the test scope.

• Verify that the test complies with industry regulations such as GDPR, or SOC 2.

Establish a Communication Plan

Good communication is crucial for a smooth testing process. This will help manage expectations and reduce any possible misunderstandings.

• Agree on the timeline for the test.

• Tell the penetration testers how they can report real-time critical findings.

Plan for Post-Test Remediation

Clients should prepare for the remediation phase of pen testing before the test begins.

• Gather resources for addressing the found vulnerabilities.

• Make an action plan for the short and long-term fixes.

• Schedule follow-up tests to ensure the remediation efforts were successful.

Penetration testing is a great step toward improving cybersecurity of your organization. Making sure you understand the purpose of penetration testing, assembling the necessary resources, and defining a clear scope can help immensely with the testing process. It is also very important to address legal considerations and establish a communication plan to make sure you are prepared for the test and its findings. These preparations maximize the return on your investment with the pen test and strengthen your company’s defense against cyber threats.

Should I tell my IT team, and how does the pen test team interact with my company's IT team or MSP?

Yes you should inform your IT team (or Managed Service Provider, MSP) about the penetration test. However, the amount of detail you provide depends on the type of test you would like to conduct.

1. If It’s a White-Box or Gray-Box Test (Cooperative Approach)

• Your IT team should be fully aware of the test and provide necessary access, such as credentials, network diagrams, and system architecture.

• The penetration testers will collaborate with your IT team to gather technical details and may conduct interviews to understand security policies.

• IT staff should monitor the test in real-time to see how their defenses react.

2. If It’s a Black-Box Test (Simulating a Real Attack)

• You may limit the information given to your IT team so they react naturally to the simulated attack.

• Only senior leadership or a designated point of contact should be aware to prevent IT staff from interfering with the test.

How the Pen Test Team Interacts with your IT Team or MSP

• Pre-Test Phase: We will request technical documentation (IP addresses, network maps, firewall rules).

• During the Test:

  • If it is cooperative, the IT team may assist in testing security controls.

  • If it is blind, the IT team will respond as if it were a real attack, and the testers will observe detection and response times.

• Post-Test Phase: The pen testing team will debrief IT staff on findings and provide remediation strategies.

Sometimes, IT teams might resist penetration testing due to concerns about disruptions or extra workload. 

• Emphasize that the goal is to strengthen security.

• Assure them that the test will be scheduled to minimize disruptions (during off-peak hours).

• Work with the pen testers to set clear boundaries on what can and cannot be tested.