This article examines how administrators in social services (n=70) and habilitation staff in healthcare (n=40) in Sweden experience difficult work situations in their daily work with people with intellectual disabilities (ID). The research aim was a) to scrutinize the most typical aspects of difficult working situations and b) to apply a comparative analysis of differences and similarities, where the respondents’ organizational affiliations are taken into account. The results are primarily based on a content analysis, although contextual standardized questions were also included. The results revealed that experiences of difficult work situations were associated with (1) structure, (2) professional role, (3) relationships, and (4) collaboration. The study also demonstrate that the respondents’ experiences of difficulties did not correspond to work dissatisfaction or unclear goals. On the contrary, handling this plurality within a specific organizational context was interpreted as an important aspect of professionalism. We argue that the different characteristics of the organizations reflect two different institutional logics. While the administrators mainly operated within an administrative logic based on a regulatory framework, the habilitation staff operated within a therapeutic logic based on a cognitive framework. The organizations different norms and rule systems, seem to have influenced when, and to what extent, everyday situations were experienced and defined as difficult when working with people with intellectual disabilities. This suggest that organizational context are important to acknowledge in order to understand professional experiences within intellectual disability services.