When penetration testing reports land on executive desks, they often represent significant investments in cybersecurity validation. And yet, many of these expensive assessments fail to deliver genuine strategic value. This leaves organizations with a false sense of security: they think they “did the deed,” but they didn’t learn anything of value. In a real sense, they’re worse off than before.
Consider the 2019 Capital One breach, where attackers exploited a web application vulnerability to access over 100 million customer records. But isn’t it ironic: Capital One had undergone multiple security assessments that failed to identify the exact misconfiguration that enabled the attack. The difference between their testing and what attackers exploited highlights a critical gap in how many organizations approach security validation.
This scenario plays out more often than you might think. Recent industry analysis shows organizations spent over $4.2 billion on security testing services in 2024, yet many walked away with little more than a compliance checkbox. Meanwhile, attackers continue to find new ways into supposedly “tested” networks.
Understanding What You’re Buying
Penetration testing, often referred to as “pentesting,” is a controlled form of ethical hacking where security professionals attempt to breach your systems using the same techniques as real attackers. But here’s the catch: not all penetration tests are created equal.
“What we’re seeing is a disturbing trend of ‘checkbox pentesting’ where firms run automated scans, dress them up in a report template, and call it a day,” says Tyler Raineri, TMG’s Manager of IT Engineering. “Real security testing requires human expertise, creative thinking, and a deep understanding of how actual attackers operate. Without these elements, you’re just getting an expensive vulnerability scan.”
A genuine security assessment should be much more than automated scanning. It’s a comprehensive evaluation that combines sophisticated tools with human expertise to reveal not just technical vulnerabilities but also gaps in processes, policies, and human behaviors that could put your organization at risk.
Most organizations need both external penetration testing to assess their public-facing assets and internal penetration testing to evaluate their core systems. While external testing examines how your organization looks to potential attackers on the internet, internal testing goes deeper, examining how an attacker might move through your network once they’ve gained initial access.
The Executive’s Penetration Testing Evaluation Framework
Before diving into report analysis, here are the key questions to ask your testing provider:
Pre-Engagement Questions:
- “Show me evidence of your manual testing methodology.”
- “How do you simulate real-world attack scenarios beyond automated scanning?”
- “What’s your process for escalating critical findings during testing?”
- “How do you tailor your approach to our specific industry and threat landscape?”
Scope and Methodology Validation:
- “Will you test both our external-facing systems and internal network?”
- “How do you assess web application security beyond standard vulnerability scanning?”
- “What’s your approach to social engineering and human factor testing?”
What Quality Penetration Test Reports Look Like
A quality penetration test report should tell a story about your security posture. Here’s what separates genuine value from expensive paperwork:
Executive Summary That Translates Risk into Business Impact
Your executive summary should read like a strategic briefing, not a technical manual. It needs to clearly articulate how discovered vulnerabilities could impact operations, revenue, and reputation. Rather than just listing technical issues, it should paint a picture of realistic attack scenarios that could affect your bottom line.
Most importantly, it should provide clear, prioritized recommendations that align with your business objectives and resource constraints. If your executive summary reads like a technical document, you’re not getting the strategic insight you’re paying for.
Technical Findings with Context and Narrative
Each vulnerability should tell a story about risk, not just technical details. Quality findings use standardized measures like the Common Vulnerability Scoring System (CVSS) to rate severity, but they also translate these scores into clear business impact. However, CVSS scores alone can be misleading—a “high” score doesn’t automatically mean high business risk for your specific environment.
The report should identify affected systems, explain realistic exploitation scenarios, and provide proper context about the risks to your organization. Most crucially, remediation advice should be tailored to your specific environment, taking into account your technology stack, resource constraints, and business requirements.
Critical Red Flags in Penetration Test Reports
Generic, Template-Driven Content
Warning signs include reports that read like they came straight from an automated tool. Real testers should explain issues in plain language specific to your organization, not generic descriptions that could apply to any company.
Isolated Vulnerabilities Without Attack Chains
If the report only describes isolated weaknesses without showing how an attacker might chain them together or move through your network, you’re likely looking at surface-level testing. Think of it like a home security assessment that only checks your front door locks while ignoring how an intruder might combine window access with a garage door opener vulnerability.
Cookie-Cutter Remediation Advice
Remediation recommendations that ignore your specific infrastructure or read like they could apply to any organization suggest a superficial approach rather than thoughtful analysis.
Missing Business Logic Assessment
Reports that focus solely on technical vulnerabilities while ignoring business process flaws represent a significant gap. Many of the most damaging breaches exploit perfectly secure systems through flawed business logic.
The Irreplaceable Human Element
Despite impressive advances in AI and automated scanning, the reality remains that even sophisticated security tools can’t replicate human creativity and intuition. This is what makes quality penetration testing invaluable.
While automated tools excel at finding known vulnerabilities, human testers discover the kinds of weaknesses that real attackers exploit most effectively. They excel at chaining together multiple seemingly minor vulnerabilities to create major security breaches—something automated tools would report as separate, low-priority findings.
Consider this real-world scenario: A skilled penetration tester discovers that your help desk staff can reset passwords with only basic identity verification—employee ID numbers and birth dates easily found on social media. Even with state-of-the-art security systems, an attacker using this simple social engineering technique could gain network access by impersonating a legitimate user. These human-centric findings often represent your greatest vulnerabilities and your greatest opportunities for improvement.
Beyond Compliance: Making Your Investment Count
Quality penetration testing delivers measurable ROI that extends far beyond compliance requirements:
Immediate Value:
- Average quality penetration test cost: $15,000-$50,000
- Average breach remediation cost: $4.45 million
- Time savings from proper vulnerability prioritization: 60-80% reduction in remediation cycles
Strategic Benefits:
- Risk-based security investment decisions
- Improved incident response preparedness
- Enhanced stakeholder confidence
- Competitive advantage through superior security posture
Engagement Excellence: What to Expect During Testing
Quality providers maintain regular communication during testing, immediately escalating critical findings rather than waiting for the final report. They should demonstrate genuine curiosity about your business operations and adapt their methodology based on discoveries made during testing.
The testing approach should be customized to your organization’s unique assets, threats, and risk tolerances—not a one-size-fits-all playbook. This includes focusing on your crown jewels and adapting the scope based on initial findings.
Your Action Plan
Whether you’re planning your first penetration testing or re-evaluating your current program, here’s your strategic checklist:
Before Testing:
- Define clear objectives beyond compliance requirements
- Identify your most critical assets and processes
- Plan remediation resources and timeline
During Vendor Selection:
- Demand evidence of manual testing expertise
- Verify industry-specific experience
- Request references from similar organizations
During Testing:
- Require regular communication and escalation protocols
- Ensure testing covers both external and internal systems
- Verify a comprehensive web application security assessment
After Testing:
- Insist all findings relate to your specific business context
- Request a clear explanation of the risk scoring methodology
- Develop a prioritized remediation roadmap
The Bottom Line
In my many decades in this industry, I’ve seen far too many organizations receive penetration tests that miss critical vulnerabilities later exploited in actual breaches. The difference between mediocre and excellent penetration testing often becomes apparent only after a real attack, when we’re called in to test environments that other firms had previously declared “secure,” only to find critical issues that automated tools simply can’t detect. At my firm, the Technology Management Group, we work to understand not only the technical landscape but the context in which our clients operate and, critically, what third-party exposure that may entail.
A mediocre penetration test is nothing but expensive paperwork. Quality testing requires significant investment—not just in the assessment itself, but in preparing for it and acting on its findings. However, this investment pales in comparison to the potential costs of an actual breach. Organizations that treat penetration testing as a genuine learning opportunity rather than a compliance exercise will experience substantially better returns on their security investments.
Explore articles by Chris Moschovitis:
The Top 5 Questions Keeping CIOs Awake at Night
Strategic Agility: Why Co-Managed IT and Cybersecurity May be the Answer
I am certified in Cybersecurity (CSX, CISM), Enterprise IT Governance (CGEIT), Data Privacy Solutions Engineering (CDPSE), and as a Certified Information Privacy Professional (CIPP/US). I am also an active member of organizations including ISACA, IAPP, and ISSA. In 2018, my book Cybersecurity Program Development for Business: The Essential Planning Guide was published by Wiley to critical acclaim. My second book, Privacy, Regulations, and Cybersecurity: The Essential Planning Guide, received an equally positive reception upon its release by Wiley in 2021. Additionally, I co-authored History of the Internet: 1843 to the Present and contributed to the Encyclopedia of Computers and Computer History as well as the Encyclopedia of New Media.
