It has long been acknowledged that gender matters in social work, not least within justice social work, given the over-representation of men within the criminal justice system. Whilst there is significant theorising about the role of gender in criminal justice, there has been little empirical examination of how social workers understand and address gender in practice. This article sets out to redress this omission by introducing a novel study of the expressed views of justice social workers (JSWs) in Scotland on gender in their work. The findings are challenging. They demonstrate that JSWs talk about gender in complex and, at times, seemingly inconsistent ways; the concept of ideological dilemmas is used as a vehicle through which to interrogate this further. Our conclusions suggest that it is not necessary to resolve the conflicts and complexities that are an inevitable response to, and expression of, the multiple and often competing discourses within which JSW practitioners operate on a daily basis, but we do need to make space for these conflicts in practice. A person-centred approach to gender, and an intersectional approach to understanding personhood, offer a way forward, allowing insight into the complex and demanding environment within which JSWs function.