In Education in prison, the Council of Europe (1990) makes a series of key recommendations, which include grounding education in prisons upon adult educational principles, developing pedagogical relationships that respond to the prisoner as a whole person, and cultivating relationships with the wider community. In critical response to the document, and partly drawing from teaching philosophy to prisoners and ex-prisoners, I develop proposals in respect of a philosophy of education for prisoners (and for others in non-traditional learning environments) in the Irish context, although it may be of broader relevance. I respond to tendencies to equate transparency and accountability with measurement rather than richer forms of evaluation and to impose models of best practice that are insensitive to local conditions. In a climate that seeks to ascertain ‘value for money’, there is a danger that an exclusive emphasis on outcomes, processes, skills and competencies may pervert the dynamic responsiveness at the heart of the pedagogical relationship. It questions the appropriateness of generalizing best practice models from other learning environments and provides a critical appraisal of the increasing tendency in certain countries to promote ‘soft’ skills and certification at the expense of education.