Many organizations overlook the true value of a comprehensive penetration test, opting instead for a baseline penetration test to save money and “check the box.” When I say, "baseline penetration test," I’m referring to one that relies solely on automated software tools to perform the penetration test. In these cases, the only human involvement is scheduling the test, compiling the results, and delivering recommendations based on what the software finds.
A comprehensive penetration test, however, goes beyond just using tools. It includes running the same automated tests and adds a manual review by a certified ethical hacker. The ethical hacker not only analyzes the software findings but also uses their expertise to dig deeper and identify things that might have been missed or could lead to further exploitation of the environment.
A Real-World Example: The Limitations of Automated Tools
Recently, a client requested a comprehensive penetration test for their internal network. After setting up our jump host, our penetration testing team initiated our usual routine of automated scanning, using AI-supported penetration testing tools. These tools found numerous vulnerabilities in the environment that could have led to a potential compromise. However, they didn’t directly compromise the domain or expose any immediate threats.
The key to what led to the compromise of their entire domain was the penetration tester’s manual analysis of the findings, which revealed a misused file share. The penetration tester reviewed the file share to find a folder containing sensitive information—potential high-value targets. They confirmed read/write access and, using a regex scan to search for common terms like “password,” “pwd,” “userid,” and “username,” found a file that contained hardcoded credentials with domain administrator privileges.
Leveraging crackmapexec, the penetration tester validated the credentials and privilege level across multiple machines. From there, they dumped credentials and hashes from the NTDS file and executed a “Pass-the-Hash” attack. Within minutes, the entire domain controller was compromised, and the environment was “Pwn3d!”
Beyond Automation: The Need for Human Expertise
Automated tools are great for identifying common vulnerabilities or misconfigurations. They quickly spot low-hanging fruit like software exploits and exposed services. However, they don’t have the capability to think creatively or analyze the findings to the level required to uncover deeper threats.
If a vulnerability is known and easily exploitable, automated tools can demonstrate that it’s vulnerable, even providing screenshots of the exploit. But they don’t dig any deeper than that. They won’t continue probing for additional threats or patterns that could lead to further compromise. A human penetration tester, on the other hand, has the flexibility to manually search for these opportunities and can use their experience to find things that automated tools might overlook.
The key difference between an automated scan and a comprehensive penetration test is human creativity and expertise involved. Penetration testers think outside the box. They use their knowledge of attack methods and real-world exploitation techniques to see things that tools miss or disregard. It’s like having a professional hacker on your side who can anticipate the moves of malicious attackers.
If threat actors only relied on the automated tools that are available today, we’d probably see a 90% drop in ransomware attacks. But that’s not how it works in the real world. Threat actors don’t limit themselves to using pre-packaged software—they use a combination of tools, creativity, and ingenuity to find new ways in.
Elevate Your Security
Automated penetration testing tools have their place. They can scan quickly, find many low-hanging vulnerabilities, and offer valuable insights into an environment's security posture. They are part of the picture, but they aren’t enough on their own. They don’t replace the value of a skilled ethical hacker.
Ultimately, organizations must recognize that cybersecurity is not a "check-the-box" exercise. It is an ongoing effort to protect against the sophisticated, multi-faceted attacks that automated tools alone cannot detect.
Ready to evaluate your defenses? Contact us today to explore our comprehensive penetration testing services and discover how we can help protect your organization from advanced threats.
