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A recent ruling by the Supreme Court of Canada has significantly altered admissibility requirements for confessions garnered during “Mr. Big” undercover operations (see R. v. Hart, 2014 SCC52). The Mr. Big technique is a Canadian invention that has been used successfully by police over the past two decades to secure confessions in hundreds of cases involving serious unsolved crimes. Despite the fact that these confessions are often supported by detailed confirmatory evidence, the technique is open to abuses and carries the risk of unreliable or prejudicial evidence leading to wrongful convictions. Using the new two-prong test of admissibility presented by the Supreme Court of Canada in R. v. Hart, this study examines concerns of reliability, prejudice, and police misconduct related to Mr. Big undercover operations through the case of a recent homicide committed by a Metro-Vancouver drug-addicted female involved in organized crime. This case comes from a larger study involving first person interviews with 87 prolific and super-prolific members of organized crime groups (i.e. crews, gangs, mafia, OMG, etc.) non-incarcerated offenders in Canada conducted between January 2013 and December 2015.