In what scenario should an organization most likely conduct penetration testing?

Conducting penetration testing is crucial when an organization aims to assess its system exposure to vulnerabilities. This form of testing simulates real-world attacks on a system or application to identify weaknesses that could be exploited by malicious actors. By actively seeking vulnerabilities, organizations can understand their security posture and take proactive measures to mitigate risks.

In scenarios where new software is being purchased, while it's important to evaluate the software's security features, penetration testing is typically unnecessary at this stage, as it is more focused on testing existing systems rather than evaluating potential products.

Similarly, during regulatory audits, the focus usually lies on compliance verification rather than targeted vulnerability assessment. Although audits might include some security checks, they do not usually encompass comprehensive penetration testing.

After the implementation of a new policy, the organization may want to ensure that the policy is adhered to, but penetration testing is generally more aligned with assessing the existing cybersecurity framework rather than the policies themselves. Testing is more meaningful when it targets the live environment and existing vulnerabilities rather than procedural compliance.

Ultimately, the primary purpose of penetration testing is to uncover vulnerabilities within the operational systems, clarifying the security weaknesses and helping to ensure that necessary mitigations are in place before an actual attack can occur.