Contra the notion of prisons as discrete, ‘hidden’ spaces, contemporary research has stressed a range of connections, transactions and exchange. The relationship between the offender and the outside communities—captured in the policy rhetoric of rehabilitation and the promotion of good citizenship—is just one of these connections. This paper explores contemporary, liberal imaginations of the ‘ideal’ citizen; it goes on to critique formal rehabilitation programmes and highlight informal mechanisms developed within the prison environment which disrupt these constructions. Ultimately, this allows a deeper appreciation of how, despite attempts to practise citizenship in an environment that renders conventional rights and responsibilities absent, the prisoner remains altogether ‘less than ideal’.