This paper seeks to take advantage of the concept of emotional capital to analyse how class is lived out through a critical educational failure by referring to the experiences of 64 community-college students in Hong Kong from a longitudinal qualitative study. Arguably an analysis of the emotions of middle-class and working-class respondents and their respective parents could enrich our conceptualization of emotional capital and theorization of its roles in class inequality/reproduction through higher education. Their parents' emotional responses to this educational failure were found to be essentially cultivating middle-class respondents' sense of entitlement to a university education but mostly challenging working-class respondents' sense of legitimacy of pursuing a bachelor's degree. This analysis unpacks processes whereby 'entitlement' and (lack of) 'legitimacy' could be passed on from parents to their children as classed emotional capital and thus suggests a mechanism of class reproduction though emotion in the field of higher education.