Between 1978 and 1989, the Connecticut State Police Department recorded outgoing phone calls in thirteen police barracks throughout the State. When this practice came to light during the investigation of a state trooper in 1988, a mystery class of plaintiffs threatened to sue for violation of the Federal Wiretap Act. The class action resulted in a $17 million settlement, in part because the State feared that it could be penalized as much as $10,000 in damages per phone call under the Wiretap Act, for a total of over $1 billion in civil liability. In 2004, the United States District Court for the Middle District of Florida entered default judgment against Michael Brown when he failed to defend against DirecTV’s civil claim for intercepting its broadcast services. Although Brown was found guilty of conversion of DirecTV’s cable signal, causing actual damages of $3,886.64, the Eleventh Circuit decided not to award liquidated damages under the Wiretap Act. DirecTV was forced to resort to other claims to recover actual damages. These cases illustrate the shortcomings of the Wiretap Act’s civil damages provision and the divergent policy concerns that plague both sides of the argument over whether liquidated damages under the Wiretap Act are mandatory.