Between 2002 and 2011, the California Supreme Court decided a series of cases that profoundly altered the ability of people convicted of indeterminate life sentences to be found suitable for parole. An inmate's vocalization of insight — in this Note taken to mean remorse, guilt, and/or shame — has become the lynchpin to freedom. This Note explores the California Supreme Court's judicial evolution on determining parole suitability, how the Court's assessment of insight can be understood through the framework of the field of law and emotion, the empirical basis for granting parole based on a positive finding of insight, and how discretionary bodies such as the California Board of Parole Hearings make assessments of insight. Ultimately, this Notes endeavors to discern whether the rhetoric of remorse and rehabilitation that insight attempts to encapsulate provides inmates with a full or a false promise for release.