Security Professionals Win $600,000 Settlement After Wrongful Arrest During Authorized Penetration Test

In a landmark case that has sent shockwaves through the cybersecurity industry, two professional penetration testers have secured a $600,000 settlement after being wrongfully arrested while conducting authorized security assessments at an Iowa courthouse in 2019.

Gary DeMercurio and Justin Wynn, then employed by Colorado-based security firm Coalfire Labs, had obtained explicit written authorization from the Iowa Judicial Branch to perform “red-team” exercises at various judicial buildings. These authorized security assessments are designed to test the resilience of existing security measures by simulating real-world attack scenarios that criminal hackers or burglars might employ.

The rules of engagement for their September 2019 operation at the Dallas County Courthouse were crystal clear, explicitly permitting “physical attacks” including “lockpicking” against judicial branch buildings, provided no significant damage occurred. This type of authorized testing is crucial for identifying vulnerabilities before malicious actors can exploit them.

However, what should have been a routine security assessment turned into a nightmare when DeMercurio and Wynn were arrested on felony third-degree burglary charges. The security professionals spent 20 harrowing hours in jail before being released on $100,000 bail—$50,000 each. Despite having written authorization and following established protocols, they found themselves facing criminal charges for performing the very work they were contracted to do.

The situation escalated when Dallas County Sheriff Chad Leonard continued to publicly allege that the men had acted illegally and should face prosecution, even after the initial felony charges were reduced to misdemeanor trespassing. This public condemnation came despite the clear contractual authorization for their activities.

“This incident didn’t make anyone safer,” Wynn stated in a powerful declaration. “It sent a chilling message to security professionals nationwide that helping government identify real vulnerabilities can lead to arrest, prosecution, and public disgrace. That undermines public safety, not enhances it.”

The reputational damage from such incidents can be devastating for security professionals. The cybersecurity industry relies heavily on trust and reputation, and being publicly associated with criminal charges—even when later dropped or reduced—can effectively end careers. More concerning is the precedent such arrests set for the entire penetration testing industry.

The incident has sparked intense debate within both the security community and law enforcement circles. Security professionals argue that these authorized assessments are essential for identifying weaknesses before they can be exploited by actual criminals. Meanwhile, law enforcement officials contend they must respond to alarm activations and apparent break-ins, regardless of the circumstances.

The specific incident at the Dallas County Courthouse occurred in the early morning hours of September 11, 2019. After discovering a side door to the courthouse unlocked, DeMercurio and Wynn followed proper security protocol by closing it to ensure it locked properly. They then used a makeshift tool to trip the locking mechanism through a crack in the door—a standard technique in penetration testing designed to verify whether doors are properly secured.

This action triggered an alarm system, alerting local authorities to what appeared to be a break-in. However, the security professionals had already taken steps to document their authorization and were prepared to explain their activities to responding officers.

The settlement, while providing some measure of justice for DeMercurio and Wynn, raises serious questions about the relationship between security professionals and law enforcement. How can authorized security assessments be conducted effectively if practitioners fear arrest and prosecution? What protocols need to be established to ensure that law enforcement can distinguish between legitimate security testing and actual criminal activity?

Industry experts suggest that this case may lead to the development of more robust communication protocols between security firms, their clients, and local law enforcement. Some propose the creation of dedicated hotlines or verification systems that would allow responding officers to quickly confirm whether a reported security breach is actually an authorized assessment in progress.

The settlement amount of $600,000 reflects not only the personal damages suffered by DeMercurio and Wynn but also serves as a warning to government entities about the importance of properly coordinating authorized security assessments. It underscores the need for clear communication channels and understanding between all parties involved in these critical security exercises.

As cyber threats continue to evolve and become more sophisticated, the role of penetration testers becomes increasingly vital. These professionals help organizations identify and address vulnerabilities before they can be exploited by malicious actors. However, this case demonstrates that the very individuals working to enhance security may themselves become targets of legal action if proper protocols aren’t followed.

The cybersecurity community has rallied around DeMercurio and Wynn, viewing their settlement as a victory not just for themselves but for the entire industry. It sends a clear message that wrongful arrests and public defamation of security professionals who are performing authorized work will not be tolerated.

Moving forward, this case is likely to influence how authorized security assessments are conducted, documented, and communicated to relevant authorities. It may lead to the development of industry-wide standards for coordinating with law enforcement and ensuring that all parties understand the nature and authorization of security testing activities.

The $600,000 settlement represents more than just compensation for two security professionals; it represents a crucial step toward protecting the vital work of penetration testers and ensuring that their efforts to enhance security are not undermined by misunderstandings or lack of proper coordination with law enforcement agencies.

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