CIMSEC – Every day, U.S. Coast Guard cutters patrol the eastern Pacific Ocean and Caribbean Sea for drug smuggling vessels, seizing more cocaine than all other American law enforcement agencies combined. Federal prosecutors then bring charges against the detained smugglers under a controversial and confusing legal regime. By analyzing the lifecycle of a case – from interdiction to detention to prosecution – this two-part article explores (1) the extraterritorial jurisdiction established by the Maritime Drug Law Enforcement Act (MDLEA); (2) the practice of detaining suspected smugglers aboard Coast Guard cutters for weeks without formal arrest; and (3) the interaction between intelligence gathering and the trial penalty. In each of these instances, a different branch of the federal government is pushing against – if not overstepping – legal constraints in order to empower the Coast Guard in the fight against maritime drug smuggling. This is a fragile system, however, and should one of these government branches become squeamish, the whole apparatus could collapse.