The aim of this study was to describe and analyze how caseworkers in the Swedish disability services deal with people disabled by road accidents. Data were collected by means of a web-based survey of 259 caseworkers, and a direct content analysis of open-ended questions was used to interpret and analyse the data. The conceptual toolbox consisted of Habermas' lifeworld-system dichotomy, social recognition, and concepts from human service organisation research. Dilemmas within the following areas were identified: interaction with the service users, experiences of communication, assessment of needs, and inter-organisational cooperation between health care and disability services. These difficulties occurred because of tensions between ‘lifeworld’ and ‘system’, and because social recognition and mutual communicative action were not easy to achieve when cognitive impairments distorted and prevented the development of an ‘ideal speech situation’. Inter-organisational cooperation was difficult because of different regulations and professional perspectives.