Regulatory pressure is widely recognized as a problem in healthcare. At first sight the solution seems simple: discard rules and give caregivers more resources to provide personalized care. Based on qualitative research in four elderly care organizations in the Netherlands, this paper shows that regulatory pressure is a persistent problem that cannot be solved on an individual level, as it results from a disconnect between the work of different actors in the healthcare system. Drawing on concepts from Organization Studies, the paper shows that the work of caregivers, healthcare managers and external actors is often decoupled. Caregivers experience regulatory pressure when the origin and function of rules are unclear. The studied care organizations are experimenting with rules, reconsidering and creating functional rules. They do so by stimulating reflection among actors in the healthcare system, thereby recoupling their work. The findings suggest that recoupling can be achieved by creating comfort zones, focusing on stimulating debate between stakeholders on the functionality and origin of rules and aligning ideas about good quality care, the role different actors can play and the rules that are needed to accommodate this.