What's Best for Your Organization?
When to Conduct Penetration Tests vs. Vulnerability Assessments
FireOak’s Recommendations for Clients
“Penetration tests” and “vulnerability assessments” are often used interchangeably, but they are distinct processes. Both have a purpose, but for most organizations, there’s a logical sequence—and not all organizations need every type of evaluation.
At FireOak Strategies, we generally recommend starting with a vulnerability assessment, addressing all the vulnerabilities identified, and then, if there’s a specific need, engaging a separate organization to conduct a penetration test.
Here’s Why
- Vulnerability Assessments come in two main forms:
- Automated (black box) scans use tools like Nessus or Qualys to scan your website externally. Results from these scans tend to be limited and typically consist of lengthy automated reports. Organizations with complex sites, sufficient internal capacity, and security expertise may consider running these scans monthly or quarterly.
- Human-powered (white box) assessments involve a thorough, internal review of your website and related systems. This approach gives a comprehensive view of your security ecosystem—including factors like server co-hosting that automated scans can’t detect. At FireOak, we use a mix of automated tools and hands-on, human analysis that surfaces vulnerabilities, explains associated risks, and provides recommended solutions. This approach uncovers issues automated tools miss and provides context for each finding.
A vulnerability assessment is only as valuable as the remediation work that follows. Your organization must address the issues identified to improve security.
- Penetration Tests simulate an intentional attack on your systems to identify vulnerabilities an attacker could exploit. These tests are often intensive, broad in scope, and potentially disruptive to staff and operations. Their results can be overwhelming and expensive to address if foundational vulnerabilities have not already been remediated.
FireOak’s Recommended Approach
- Start with a human-powered vulnerability assessment.
- Focus on specific areas—such as your website—address findings, and remediate issues.
- Broaden to a holistic information security assessment covering Microsoft 365, Google Workspace, Salesforce, and your organization’s full technical stack, including data governance and operational security procedures.
- Use these non-destructive external assessments to build maturity in your information security program.
- Only after addressing identified vulnerabilities and establishing a mature security program should you consider a penetration test.
- Penetration tests should be conducted by a different firm than the one that performed the vulnerability assessment, to ensure independence and objectivity.
The goal is to strengthen your organizational security in a practical, mission-aligned way. For most organizations, a penetration test is not the first step and can create unintended consequences if performed too early. Begin with a thorough vulnerability assessment.
