County Pays $600K to Wrongfully Jailed Pen Testers

Two penetration testers (formerly of Coalfire, now leading Kaiju Security) received a $600,000 settlement after being arrested during an authorized 2019 physical red team at the Dallas County, Iowa courthouse, despite presenting valid contracts and initial police acknowledgment. The article details the inter-agency conflict that led to burglary charges, the multi-year legal and career fallout, and practical takeaways on managing risk in red team operations—highlighting the trade-offs of pre-notification, the importance of meticulous documentation, and the reality that misunderstandings can persist even with prior law enforcement coordination.