This Article blends theory and a close look at real-world practices to examine five critical and interrelated aspects of how regulatory design influences the pursuit of regulatory goals. First, it explores the use of three foundational legal mechanisms of the administrative state – rulemaking, enforcement adjudication, and permitting (sometimes referred to as licensing). Second, it evaluates the roles that different actors play in the implementation of regulatory programs. Third, it identifies available governance tools that may be available for use by different regulatory actors in the exercise of available legal mechanisms. Fourth, the Article considers the goals an agency is supposed to achieve. In the setting we study (environmental regulation), tools and outcomes or goals may be conflated because of the challenges of evaluating ultimate goals and their relation to agency strategies. And, finally, the Article explores the possible salience of key features of agency enabling statutes that may influence or guide agency behavior. Our thesis is that regulatory effectiveness, and indeed agency legitimacy more generally, is influenced by the interactions of legal mechanisms, actors, tools, goals, and statutory authorization and constraints. Policymakers designing regulatory programs should take into account all five elements and how choices concerning each is likely to affect the capacity of the others to impact regulatory success or failure. This Article and a related piece provide a case study of the efforts of one agency, the U.S. Environmental Protection Agency (EPA), to use the three foundational administrative law mechanisms identified above to enhance its enforcement and compliance promotion efforts through a novel approach it called Next Generation Compliance (Next Gen). The heart of this initiative involves increased use by an array of public and private actors of tools that include advanced monitoring technologies, enhanced transparency, improved communications technology (particularly electronic reporting), other innovative enforcement strategies (such as third-party monitoring), and “better” (easier to understand and comply with) regulations. Our case study examines how EPA has used its foundational administrative law mechanisms to increase use of these tools, with the ultimate goal of improving compliance with regulatory requirements. We explore the advantages and disadvantages of reliance on each mechanism in a novel effort to consider the interactions of legal mechanism choice by evaluating the roles of different regulatory stakeholders and the choice of available governance tools. The two articles begin to fill significant gaps in the compliance literature concerning the extent to which legal mechanisms, the actors capable of implementing them, governance tools and objectives such as improved monitoring and enhanced transparency, and nuances in statutory approaches may influence agency behavior and outcomes.