This article explores a zone of conflict and a demonstrable gap in perceptions of casework and public services in Denmark between service users with disabilities and caseworkers. First, based on a descriptive analysis of responses from two surveys, one of service users with disabilities (N = 1,427) and one of caseworkers from four human services departments (N = 428): the ‘Job Centre’, ‘Adult Disability’, ‘Children & Families’ and ‘Health’, we find significantly different levels of trust in the services between the two groups. Second, drawing on semi-structured interviews with service users (N = 20) and municipal caseworkers (N = 10), we explain this difference through the identification of a series of intersecting dilemmas that create barriers and conflict. Overall, a thematic analysis of the interviews shows that the trust between caseworkers and people with disabilities is influenced by a complex interplay of individual, relational, situational and organisational factors. Knowledge gained from this study will help shape municipal service provision for people with disabilities, by supplementing the experiences and perspectives of caseworkers and service users and by directing attention to core dilemmas in social work that challenge trust and service user involvement.