In recent years, there has been a growing investment in service design to transform healthcare. While existing literature describes several trade-offs related to catalysing change in complex settings, there has been little understanding to date ofhow practising service designers in healthcare respond to these choices. There is a need to learn more about how these practitioners navigate their positioning, achieve change and influence healthcare organisations. Bringing forward the situated and contextual knowledge of practitioners about their approach is critical for advancing the emerging practice of healthcare service design. This chapter explores and weaves together the narratives of seven practitioners who employ service design within the healthcare context. What is revealed from this explor- ation is an “in-betweenness”—where practitioners cope with and make use of contradictions through three compound approaches in healthcare service design. We have labelled these approaches as (1) enacting the insider-outsider, (2) creating radical-incremental change, and (3) catalysing top-up dynamics. The dialogue that emerges through this chapter deepens the understanding of how service designers approach their work within the existing dynamics of social and organisational hierarchies while co-creating change with and within healthcare organisations. Through reflection on the composite nature of healthcare service design approaches, this research offers a grounded perspective on service design practice in healthcare and sheds light on possibilities for future research.