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Penetration Testing

What is penetration testing?

Penetration testing is a series of attack simulations targeted towards organizations. They use the same techniques that malicious actors would use but are authorized by the organization. Penetration tests are crucial to testing the robustness and resilience of an organization’s security posture as they are designed to identify weaknesses within the organization.

Types of Penetration Test

Not all penetration tests serve the same purpose. It is important for leaders to assess gaps and identify which would be most beneficial to their organization. Different penetration tests have different benefits and drawbacks.


Blackbox testing is when the penetration tester is placed in the role of the average hacker, with no internal knowledge of the target system1. Organizations do not provide testers with architecture or code. Testers must rely on their ability to dynamically analyze client organizations. Blackbox testing is the most comparable to common real-world threat campaigns. With that said, there are risks to blackbox testing. Organizations seeking blackbox testing need to scope their tests very thoroughly. If the test is not well scoped, there is a risk the tester of causing damage to the production infrastructure or the code.



Greybox testing uses some documentation of client environments. During a greybox test, penetration testers may get access to high level architecture documents or basic network inventories. Greybox testing allows testers to focus their efforts, providing greater utility at lower cost than blackbox penetration testing. The caveat to greybox penetration testing is that it is less realistic than a blackbox or whitebox test.


Whitebox testing gives detailed information about the systems or applications being tested. Whitebox testing simulates testing from the perspective of a member of internal staff or personnel. With the rise of insider attacks, or staff with privileged access compromising organizations, whitebox testing is increasingly important to mix into most organizations’ penetration testing strategies.

Why is penetration testing important?

Penetration testing is an intrusive practice, as the name suggests. With the intrusive nature of penetration tests, testers get an intimate understanding of the organizations they engage with. Penetration testers can use their experience and identify gaps beyond what insiders may be able to identify alone. Penetration tests allow organizations to make informed security decisions.


Compliance is a security principle by which organizations provide assurances to their internal and external stakeholders that they have protected their organization and information that other organizations trust them with. Penetration testing is a requirement for organizations striving to achieve compliance to several industry-recognized certifications.

Securing the Organization

The average cost of a breach is $2.1M USD. In addition, the cost per stolen record has increased to $148 USD per record2. Proactively placing security measures to address vulnerabilities reduces the likelihood of a breach or stolen records being realized. This is best achieved by leveraging skilled security personnel in addition to implementing technologies and practices that can be maintained. With that said, experienced security professionals are difficult to come by. Penetration testing is a good practice to leverage the experience of external security professionals to augment existing resources.

Penetration testers are highly skilled personnel who must identify gaps in implemented controls within organizations. Skilled penetration testers can identify oversights in security implementations so they are not exploited by malicious actors. In addition, penetration testers typically uncover “unknown unknowns.” Experienced penetration testers are able to provide risk-based feedback to help organizations roadmap which controls to prioritize.

2 IBM: Cost of a Data Breach 2022 Report


Organizations with strong penetration testing practices provide their clients with assurances that they are making continuous improvements to their security posture. In addition, they illustrate that they are making additional commitments to identify and fix vulnerabilities that may impact customers.

Methodologies and Procedures

Small and medium organizations often struggle with the preparation process to get ready for their penetration tests. Penetration tests follow a common approach. The reason there is a common approach is to help define repeatable processes while minimizing the impact of testing to the organization being tested. The steps are as follows:

  1. Information Gathering
  2. Analysis and Planning
  3. Vulnerability Identification
  4. Exploitation
  5. Risk Analysis and Remediation
  6. Reporting and Lessons Learned.

Organizations can modify and adjust the procedures to be catered toward their business processes, but they will typically follow the methodology listed. As organizations grow, they should consider adopting threat modelling and threat identification processes such as the Mitre Att&ck framework or Cyber Kill Chain.


Regardless of industry or size, organizations should consider including penetration tests as part of their security strategies. Penetration tests should be scoped well with the guidance from security experts to ensure they provide utility without negatively impacting the organization being tested. Penetration tests help organizations create roadmaps to improve their resilience while illustrating commitment to partners, clients, and staff. Organizations should consider building penetration tests into their security programs early so they can scale with the increasingly complex challenges they face as part of the cybersecurity landscape.