This study focuses on street-level managers’ (SLMs) compliance with COVID-19 measures in Switzerland, Germany, Italy, and Israel, in order to better understand their role during policy implementation. Responsible for the direct delivery of public services, street-level organizations serve as the operational arm of the state in general and as the frontline of government policy in times of crisis. SLMs who occupy the top managerial tier within their organization are understudied, although they exert a significant influence on everyday public life. The data comprise 399 “compliance stories” based on interviews with managers in nurseries, schools, health care and welfare offices, police stations, and care homes. Using “codebook thematic analysis,” we identify various levels of (non)compliance and several prominent explanatory factors that shape (non)compliance. Data show that even when asked about particularly challenging measures, managers reported that their organization had been noncompliant (either full or partial) in only about a quarter of the stories. Three influences emerge as primary barriers to compliance—a lack of resources, managers’ relationships with clients, and the perception of the measure’s effectiveness. Emphasizing that SLMs often act as local policy entrepreneurs using their discretion to solve problems and serve the public, our findings further demonstrate the crucial role they play in shaping the face of the government for the people.