One in seven people in prison in the US is serving a life sentence, and most of these “lifers” will someday be eligible for discretionary parole. But little is known about a key aspect of parole decision‐making: remorse assessments. Because remorse is a complex emotion that arises from past wrongdoing and unfolds over time, assessing the sincerity of another person's remorse is neither a simple task of lie detection, nor of determining emotional authenticity. Instead, remorse involves numerous elements, including the relationship between a person's past and present motivations, beliefs, and affective states. To understand how parole board members make sense of remorse, we draw on in‐depth interviews with parole commissioners in California, the state with the largest proportion of parole‐eligible lifers. We find that commissioners' remorse assessments hinge on their perceptions of lifers' relationships to law and carceral logic. In this way, relational legal consciousness—specifically, second‐order legal consciousness—functions as a stand‐in for the impossible task of knowing another person's heart or mind. We distinguish relational from second‐order legal consciousness and argue that understanding how they operate at parole hearings reveals the larger import of relational legal consciousness as a mechanism via which existing power relations are produced and reproduced, bridging the legal consciousness and law and emotion literatures.