In the age of digitalisation social work is transforming. With increased use of information systems social workers are meeting new professional challenges. In this paper we report findings covering a nine-year longitudinal study on critical issues in the use of a Case Management System in a Swedish social work agency. The study includes a stakeholder based evaluation, interviews and document analysis. Comparing the evaluation findings with literature helped us identify six areas in need of intensified research: i) Usability and interface design ii) Mismatch between social conceptualisation and system conceptualisation of the case iii) Skills and training for information systems use iv) Statistical production for accountability and quality assurance v) Terminology for interpersonal understanding vi) IT Governance. As can be seen from the areas above, this kind of research depends on professional knowledge from the social work field - but also from the field of information systems. Hence, we suggest deeper collaboration between the two areas of knowledge in order to scrutinize the complexity of social work information systems. Clearly the intersection of social work and information systems is a neglected research area and we attempt to contribute by providing guidance for intensified research and practical knowledge generation.