Planning Your First PenTest


In today’s digital age, cybersecurity has become a top priority for businesses of all sizes. No company is immune to potential cyber threats. Small businesses and start-ups are appealing targets for cybercriminals because of their perceived vulnerability. Therefore, it is crucial for them to assess and strengthen their cybersecurity defenses. One effective way to achieve this is by conducting a penetration test. In this blog post, we will provide a guide for small companies to plan their first penetration test. 

 1. Understanding Penetration Testing

Penetration testing, commonly known as a pentest, is a safely simulated attack on your company’s computer systems. Its purpose is to identify vulnerabilities that hackers could exploit. By mimicking the actions of real-world attackers, the pentest aims to show the weak spots in your security. The basic idea is to uncover the potential weaknesses and fix them, before malicious actors can exploit them.

 2. Defining Objectives and Scope

Before initiating a penetration test, it is essential to establish clear objectives. Determining the objective of a pentest is about deciding which information assets need to be safeguarded. These could be PII, health data, financial data or another company’s commercially sensitive data, among many others. Often, such sensitive data is regulated (E.g., GDPR, HIPAA, PCI-DSS) or are subjected to special clauses in contracts and NDAs.

After determining the data to be safeguarded, you should then determine the pentest scope. Tracing the path of the information assets through your systems (follow the data) is helpful for determining the pentest scope. These would normally be your network segments, file/database servers, web applications, or employee devices. Securing the perimeter with the outside world (i.e., the Internet) can be prioritized over testing the security of your internal network. Therefore, it makes more sense to test the Internet exposed systems first, and then proceed with the assets on the internal network.

At Sistematik, we provide free consulting to companies, to help them determine their pentest scope and plan their pentest. You can book a 40-minute session for free here or here, and talk to an expert.

 3. Choosing the Right Penetration Testing Service Provider

Working with an experienced penetration testing service provider is crucial. Look for the following items:

  • They should work methodically. Ask if they follow a standardized checklist during fieldwork.
  • They should present a clear time plan for their activities. This should include pentest preparation, fieldwork, remediation process, verification of fixes, and close-out.
  • They should produce a high-quality documentation of their results. The report should provide vulnerability details, present examples, and recommend applicable, cost-effective solution advice. Ask for a sample report.
  • They should establish regular communication during the fieldwork, such as regular progress updates. Ask them to provide regular status updates during the fieldwork.

Also, it is a good practice to have at least a brief meeting with the team to make sure that they have a basic understanding of your work and your systems.

 4. Conduct a Pre-Assessment

If there are missing patches, out-of-support software or known vulnerabilities, it would make sense to fix them before the pentest. This way, the pentest team would not spend time on issues that you already know.

 5. Communication and Stakeholder Engagement

Inform your employees and relevant stakeholders about the upcoming penetration test. Emphasize the importance of the exercise and communicate that it is a proactive measure aimed at enhancing cybersecurity. Encourage employees to report any suspicious activities during the test to ensure a smooth and accurate assessment.

 6. Preparation for the Pentest

While a pentest is a simulated attack with tools and techniques that real-world attacker use, executing it safely is also paramount. Application owners must put in place certain safety measures before test execution. These are:

  • Preparing the test environment.
  • Making the access arrangements.
  • Preparing sanitized test data.
  • Creating the necessary test accounts.
  • Making an application tour with the test team (optional).
  • Highlighting the scope exceptions to the pentest team.
  • Highlighting the 3rd-party integrations of the target systems.

Sistematik’s detailed documentation for the pentest engagement preparation is accessible here.

 7. Penetration Test Execution

Once all preparations are in place, and the scheduled date arrives, parties would kick off the pentest. The duration of the test will depend on the complexity of your systems and the agreed-upon scope. The pentest team will go through their checklist, identify vulnerabilities, and document the results. One important aspect during the pentest is open communication. It allows tracking the progress, and ensures promptly reporting of any critical issues.

 8. Analyzing the Results

After the penetration test, the pentest team will compile a detailed findings document. The findings document should include the identified vulnerabilities, severity levels, and recommended mitigation measures. Thoroughly review the report, paying attention to both critical and low-risk vulnerabilities. Prioritize the mitigation of high-risk vulnerabilities and develop a plan to address them promptly. Discuss with the pentest team if any detail is unclear.

 9. Implementing Remediation Measures

Work closely with your IT team or service provider during the mitigation. Make sure they can consult the pentest team whenever needed. Also, inform the pentest team about the completion date of the mitigations, and when they can perform the verification of your fixes.


For small companies, investing in a penetration test is a proactive and necessary step towards fortifying cybersecurity defenses. By identifying and addressing vulnerabilities before cybercriminals can exploit them, you can safeguard your sensitive data and protect your business from potential reputational and financial harm. Remember, cybersecurity is an ongoing process, and regular assessments and improvements are essential to stay one step ahead of ever-evolving threats.