Purpose This study aims to explore the ways in which young people and prison staff (Prison Officers) within a youth custodial establishment experience empathy. Previous research tends to view empathy as a stable trait and one which people can develop through individual-centred therapy. There has been little consideration of the impact of relationship factors and context in relation to empathy experience and expression. The current study aims to address this by exploring the role of the custodial context in shaping empathy, including the potential impact of relationships, environmental factors and culture. Design/methodology/approach A qualitative approach was used to enable breadth and depth in the exploration of this area. Individual, semi-structured interviews were carried out with a purposive sample of three young people and three Prison Officers. Data was analysed using inductive thematic analysis informed by the guidelines of Braun and Clarke (2006) and King and Horrocks (2010). Findings Constructed themes included “constructions of empathy”, “recipe for empathy”, “institutional investment”, “the value of empathy” and “doing empathy”. Together, they provide detailed insight into the interplay of personal and wider contextual factors influencing the experience of empathy in a custodial setting. The findings suggest that the way in which young people and staff experience empathy in the custodial environment is unique. The findings suggest that empathy takes place within the context of relationships and is influenced by the nature of those relationships, along with the wider social context within which it occurs. Practical implications The findings of the current study support a move away from understanding empathy as an individual personality trait and instead viewing it as a dynamic experience that is changeable based upon the relationship and the context within which it occurs. The findings suggest that interventions aiming to develop empathy should look beyond the level of the individual and the relationship and focus upon developing environments that are supportive of empathy. Originality/value This study provides unique insights into the subjective experience of empathy in a custodial setting, presenting as one of the first to take a more holistic approach to understand this phenomenon.