Penetration Testing: The Only Way to Know If You’re Actually Secure

Penetration testing isn’t just about checking a box - it’s about answering a fundamental question: If someone tried to break in right now, could they? It’s the difference between assuming your defenses work and proving they do. While vulnerability scans flag known issues, pen testing simulates real-world attacks to uncover unknowns - misconfigurations, unauthorized access points, and open ports that no checklist will catch.

Whether you’re preparing for an audit, validating a recent deployment, or simply trying to sleep better at night, pen testing helps to give you clarity. It’s not just technical - it’s strategic.

When “Secure” Isn’t Secure Enough

Cybersecurity concerns have continued to grow and are a big (Huge? Monstrous?) concern for many. It is also very complicated, confusing and unsettling. And the approach needs to be thought of as a circle instead of a straight line - you always need to loop back to test and improve. So, even if you think you are covered, you do have to test yourself and there are many cases that exemplify that thought.

Think of the mid-sized financial services firm that was confident in its perimeter. Firewalls were locked down, MFA was enforced, and endpoint protection was humming. But during a black-box pen test, the team discovered an exposed dev server with default credentials. Within hours, they had lateral movement, access to client data, and a simulated ransomware payload ready to deploy. The firm had no idea that server even existed (Hmmmm – time to think about doing an Asset Inventory?).

In another engagement, a healthcare provider commissioned a social engineering test. The red team posed as IT support and convinced multiple employees to share credentials over the phone. Within minutes, testers accessed patient records - no malware, no exploits, just human trust.

These cases highlight why pen testing matters: it reveals what your policies, tools, and assumptions miss.

And sometimes, the threat isn’t malicious - it’s accidental. After all, who hasn’t seen WarGames? A teen, poking around to hack into and play an unreleased video game, “stumbles” into a military supercomputer and unknowingly triggers a nuclear simulation…. The takeaway? Even well-defended systems can still be vulnerable. Pen testing helps you find the doors you didn’t know were open.

PW: Joshua

Would You Like to Play a Game?

Pen testing isn’t just about finding flaws - it’s about running the simulation before someone else does. Think back to WarGames, where the machine can’t tell the difference between a game and a real threat. We’ve come a long way since then, but the underlying issue still applies: many organizations assume compliance equals protection. They check boxes - but not necessarily defenses. You do need to consider what type of pen testing is right for your organization.

Sometimes, internal teams or external assessors may be conducting tests that check a compliance box, but do not properly test your security. Black box, white box, gray box, red team, purple team, etc. - if the scope’s off, critical assets and flaws may get missed. Dev servers, SaaS integrations, forgotten endpoints… they’re often left out of the picture. The result? A false sense of security.

Then there’s the reporting gap. Findings might be too vague for remediation teams or too technical for leadership. Fixes stall. Risks linger. And the organization stays reactive - always one step behind.

Pen testing changes the game. It reveals what your policies, procedures, tools, and assumptions miss - and gives you a chance to respond before it’s real.

What Should You Do About It?

There’s no one-size-fits-all approach to pen testing, but here are the most effective paths forward:

• Manual Testing: Ethical hackers simulate real-world attacks using custom tactics. Ideal for high-risk environments or nuanced systems.

• Cybersecurity Tool-Based Testing: Platforms like Kali Linux, Metasploit, Burp Suite, and automated solutions like Horizon3.ai offer scalable, repeatable assessments.

• Hybrid Approaches: Combine manual expertise with automated tools to balance depth and efficiency. This is often the most pragmatic route for mid-sized organizations.

• Third-Party Assistance: If your team lacks the skill set - or simply needs an outside perspective - engage a firm that specializes in penetration testing. They bring credibility, experience, and often a more structured approach to scoping, execution, and reporting.

Case Study: How Cox Enterprises Uses Pen Testing to Stay Ahead of Threats

Cox Enterprises, a $19.2 billion media and broadband company, implemented continuous penetration testing to proactively identify and remediate vulnerabilities across its vast infrastructure. In one engagement, over 480,000 endpoints were assessed, uncovering exposures that traditional scans had missed. The company leveraged a combination of machine learning and ethical hacking to:

• Accelerate vulnerability remediation in real time

• Provide C-level executives with actionable risk context

• Reduce exploit windows during high-risk periods, including national elections and targeted ransomware campaigns

This approach helped Cox shift from reactive security to a proactive, threat-informed defense strategy.

Pen Testing: Getting it Done

Before jumping into execution, organizations should clarify a few key factors:

• Why are you testing? Is it for compliance (e.g., PCI-DSS, SOC 2), security validation, cybersecurity insurance requirements, or peace of mind before a major release or acquisition?

• When does it need to happen? Are you facing a regulatory deadline, preparing for an audit, or trying to meet a contractual obligation before closing a deal? Also, consider whether this will be a one-time event, an annual requirement, or part of a more frequent cadence.

• What needs to be tested? Define the scope clearly. Consider the number of domains and IPs, whether your environment is on-premises, cloud-based, or hybrid, and whether wireless networks or mobile apps are in play. Don’t overlook phishing simulations or social engineering - these often reveal the most exploitable gaps.

• What’s the right approach? Choose based on your risk profile, budget, and maturity. A black-box test may simulate external threats, while a white-box test validates internal controls (we’ll discuss the various approaches more in a future blog post). Your reasoning for testing should guide the scope and depth.

• How will you execute? Engage the right testing method - internal, external, tool-based, or hybrid. Consider third-party specialists for credibility and depth.

• What happens after? Ensure findings are translated into clear reports and prioritized remediation plans. External partners can assist with both technical fixes and executive-level summaries.

If your team needs help scoping, executing, or interpreting a pen test, we’re here to support you (click the button above or complete the form below). Whether you’re starting from scratch or refining an existing program, we can help you align testing with your business goals, compliance needs, and risk appetite. Let’s make sure your next test delivers more than findings - it delivers confidence.

Next Up in the Pen Testing Blog Series

In future blog posts, we’ll explore the various Pen Testing Approaches - how each approach works, what they reveal, and how to choose the right one for your organization.

Disclaimer: This article was created with some AI assistance, but edited, reviewed and fact-checked by a real person.