A continuous expansion of higher education has made it possible not only for more students to get straight into university, but also for more students to obtain a university place at their second attempt immediately after their first attempt fails. However, the educational experiences of students who seek such a second chance have been under-examined. In filling this empirical gap, this book offers an application of Bourdieu’s analysis of class reproduction through education (together with his three concepts of habitus, cultural capital, and field, and the concept of emotional capital derived from an extension of his framework) to make sense of educational experiences of 64 community-college students who seek such a second chance in Hong Kong.The option of community college as a second chance became available in Hong Kong in the year 2000. The book explores how specific characteristics of community college in Hong Kong impact on the ways in which respondents of the middle and working classes see and feel about their selves throughout the course of pursuing this second chance. It also revisits Bourdieu’s framework and suggests the possibility of theorising an observed class contrast in orientation to making sense of (academic) challenges posed in educational contexts as a form of classed habitus of middle-class situational interpretation as opposed to working-class direct understanding.