Emotional literacy as a skill in probation practice requires an ability to understand and regulate one’s own emotions, in order to be responsive to the emotions of others. The concepts and methods used in this article arise from research by Charlotte Knight for a PhD on emotional literacy in work with high-risk offenders and the practice of Panna Modi, who works as a probation officer in a sex offender treatment unit with low, medium and high risk offenders. Reference is made to the case studies of two men who were participants in a Community Sex Offender Groupwork Programme (C-SOGP) and examines some of the emotional processes and skills involved in work with them.