Judgments about a youth’s level of remorse are frequently used to make important decisions in the juvenile justice system that can have serious consequences to the person. Unfortunately, little is known about these ratings and what factors may influence them. In a sample of 325 1st-time youth offenders who were arrested for offenses of moderate severity, we tested whether probation officers’ ratings of an adolescent’s remorse soon after arrest were associated with the youth’s self-report of showing a callous and unemotional interpersonal style, being arrested for a violent offense, and several demographic and background characteristics (e.g., age, race, socioeconomic status [SES], and intelligence). Our analyses indicated that both arrest for a violent offense and the adolescent’s self-reported level of callous–unemotional (CU) traits were associated with probation officers’ ratings of remorse. Further, youth age, SES, and intelligence neither were associated with these judgments nor moderated the association between CU traits and probation officers’ ratings of remorse. However, youth race or ethnicity did moderate the association between CU traits and judgments of remorse, such that Latino youth who were high on CU traits showed a very low probability of being rated as remorseful.