County Pays $600K to Wrongfully Jailed Pen Testers

Seven years after their arrest, two white‑hat penetration testers have received a $600,000 settlement in Dallas County, Iowa. Gary De Mercurio and Justin Wynn were arrested in 2019 after testing the alarm system at a Dallas County courthouse as part of a contracted security evaluation, despite having legal clearance from the state and initial police sign‑offs.

They were jailed overnight following a county sheriff’s decision, with bail set at $50,000 each, and faced a protracted legal fight before the settlement was reached. The testers, who were employed by Coalfire at the time and are now leading Kaiju Security as chief executive and president respectively, describe the outcome as bittersweet and not fully restorative.

The case has been cited as highlighting the risks security professionals can face during red‑team exercises, and illustrates the tension between realistic testing and lawful, accountable engagement. According to Dark Reading, the settlement marks a long‑overdue resolution for actions many described as a Kafkaesque nightmare.