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Algorithmic management (AM)’s impact on worker well-being has led to calls for regulation. However, little is known about the effectiveness and challenges in real-world AM regulation across the regulatory process—rule operationalization, software use, and enforcement. Our multi-stakeholder study addresses this gap within workplace scheduling, one of the few AM domains with implemented regulations. We interviewed 38 stakeholders across the regulatory process: regulators, defense attorneys, worker advocates, managers, and workers. Our findings suggest that the efficacy of AM regulation is influenced by: (i) institutional constraints that challenge efforts to encode law into AM software, (ii) on-the-ground use of AM software that shapes its ability to facilitate compliance, (iii) mismatches between software and regulatory contexts that hinder enforcement, and (iv) unique concerns that software introduces when used to regulate AM. These findings underscore the importance of a sociotechnical approach to AM regulation, which considers organizational and collaborative contexts alongside the inherent attributes of software. We offer future research directions and implications for technology policy and design.