Over the past few decades, the large scale of imprisonment and the heavily-adopted punitive approach as a way of responding to crime have engendered widespread concerns among the public and academia in the UK. Whereas there have been a good number of studies that have investigated their underlying sociological causes and elaborated a variety of accounts of how such phenomena are historically configured and how they may be moderated or reversed, the normative dimensions of the current imprisonment complex have not yet received sufficient examination. This particularly regards the understanding of the tensions between the aspiration for a universal ideal of imprisonment and the reality of highly diverse and fragmented post-welfarist approaches in the incarceration field. This thesis tries to uncover and account for the dilemmas and problems in the normative sphere of incarceration in the UK. In doing so, it elaborates the analytical-evaluative framework based on the concept of introspective normativity.