This paper examines the tension between macro level regulation and the rule breaking and rule following that happens at the workplace level. Using a comparative study of Canada, Norway, and Germany, the paper documents how long-term residential care work is regulated and organized differently depending on country, regional, and organizational contexts. We ask where each jurisdiction's staffing regulations fall on a prescription-interpretation continuum; we define prescription as a regulatory tendency to identify what to do and when and how to do it, and interpretation as a tendency to delineate what to do but not when and how to do it. In examining frontline care workers' strategies for accomplishing everyday social, health, and dining care tasks we explore how a policy-level prescriptive or interpretive regulatory approach affects the potential for promising practices to emerge on the frontlines of care work. Overall, we note the following associations: prescriptive regulatory environments tend to be accompanied by a lower ratio of professional to non-professional staff, a higher concentration of for-profit providers, a lower ratio of staff to residents and a sharper division of labour. Interpretive regulatory environments tend to have higher numbers of professionals relative to non-professionals, more limited for-profit provision, a higher ratio of staff to residents, and a more relational division of labour that enables the work to be more fluid and responsive. The implication of a prescriptive environment, such as is found in Ontario, Canada, is that frontline care workers possess less autonomy to be creative in meeting residents' needs, a tendency towards more task-oriented care and less job autonomy. The paper reveals that what matters is the type of regulation as well as the regulatory tendency towards controlling frontline care workers decision-making and decision-latitude.