Why PEN Testing Delivers Greater Value With Cyber Deception

Annual penetration testing (PEN test) is a critical component of any organization’s robust cybersecurity strategy. PEN testing is important because it is designed to identify vulnerabilities before malicious actors can exploit them. 

Penetration testing allows defenders to identify and address vulnerabilities before they can be exploited. The effort required to remediate these issues often represents a significant portion of an IT team’s annual budget and workload. Given that investment, it becomes essential to maximize the value of each test. 

A PEN test uses an expert engineer or an automated platform, to probe the network for weaknesses. At the end of the test, an expectation is set about the security of the network and what actions must be completed to address any weaknesses and gaps uncovered during the test. The length of a PEN test will vary from hours to weeks and even months. When an automated platform is used, PEN tests can be run at will covering a wide variety of criteria. 

Many, if not most, organizations will contract with an outside party to conduct the PEN test. It’s easy to see why. A functioning internal team will cost at least $500,000 in salaries and tools. It is not hard to create a team that surpasses $1 million in annual costs which often exceeds the entire cybersecurity budget of most companies.  

In my estimation, as many as 85% of organizations are using external PEN testers that charge around $8,000 per test for small projects. Automated PEN test platforms can cost about twice that amount, depending on the size of the organization. 

Inside a real-world PEN test engagement

In many organizations, the PEN testers are referred to as the Red Team. The internal cybersecurity/IT team is called the Blue Team defenders. They do not need to be involved during the testing. 

Let’s use a real world example where ACME Inc. has contracted with TeamRed, a fictitious PEN testing company, to conduct a series of PEN tests around its network over a two-week engagement. Planning for TeamRed will including scoping discussions and the sharing of basic information about the network infrastructure they are testing. 

TeamRed begins its “attack” and meticulously logs its activity over the course of the two-week testing period. Defenders, ACME’s Blue Team, may or may not notice any activity on the network. It is certain that TeamRed will make every effort to go undetected. 

The PEN test will look for as many weaknesses as it can find. TeamRed is not just looking for unpatched vulnerabilities, weak credentials, or poor policies. TeamRed is looking for overall cybersecurity weaknesses including ACME’s ability to detect activity. 

At the end of the test, TeamRed presents its results in a lovely report with matching graphs and charts. Of course, they also present a bill. For a two-week PEN test, I estimate the bill to be at least $25,000. ACME looks at the report’s conclusions and asks themselves: 

• Although some of TeamRed’s activity was detected, how much activity was not detected?
• What tools can be used to see exactly what tactics, techniques and procedures (TTPs) TeamRed used during its time in the network?
• Is it possible to get more from the $25,000 outlay through real-time learnings rather than a post-mortem review of a report?
• What would make this a complete Purple Team (Red Team and Blue Team working together) test?

Enhancing detection and response capabilities 

To help ACME address its questions, let’s take a look at what cyber deception techniques bring to the PEN test experience. Cyber deception uses a mixture of “deceptive artifacts” that are placed around an environment and designed to attract and occupy attackers. 

Using cyber deception, PEN tests can be made more valuable in three ways: 

1. Provide advanced, substantive and realistic threat intel. 
2. Confirm the thoroughness and effectiveness of the PEN test itself. 
3. Confirm the realism, depth, and effectiveness of the cyber deception solution. 

ACME’s goal is to make the PEN test as realistic and comprehensive as possible. Only by using the most advanced defensive strategies can TeamRed simulate the most advanced attacks. 

Cyber deception introduces dynamic and adaptive elements into the network environment, allowing penetration testers to interact with deceptive assets in addition to production assets. The use of known vulnerable assets (the decoys) allows for confirmation of the effectiveness of the PEN test. And the test will also confirm the viability of the deception design by catching the PEN test activity. 

Without cyber deception in place, it would be nearly impossible to deconstruct TeamRed activities on real devices. Even if it were possible, it would be costly in both time and technology. The Blue Team would need to analyze logs, search for malware, and dig deep into its own environment. Cyber deception, particularly the decoys, are specifically designed to track activity and provide a wealth of data to the defender including telemetry, keystrokes and even credentials used in the test. 

Additionally, the deception service can implement elements of “moving target defense” by changing the makeup of subnets before and during the test. This keeps TeamRed engaged and challenges them to use the most sophisticated reconnaissance techniques, thereby improving the overall quality of the test by simulating the most advanced attacks. 

Enabling continuous improvement 

The intelligence gathered from deception-based interactions during penetration tests provides actionable insights into how attackers move through the network, which security controls are bypassed, and how quickly detection occurs.  

The deception service will inherently provide high-quality data in an easily consumable format allowing defenders to assess the test methods. This continuous feedback loop empowers organizations to refine their security posture, adjust deception placements, and improve incident response protocols over time. 

Integrating cyber deception into annual penetration testing creates a more realistic, dynamic, and challenging environment for security assessments. By leveraging cyber deception, organizations can better evaluate detection capabilities, improve response readiness, and identify both technical and human vulnerabilities — ensuring a stronger, more resilient cybersecurity posture.