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This Article discusses systems thinking as an innovative approach to contextualizing legal advocacy. Systems thinking, a paradigm that emphasizes universal interconnectivity, provides a theoretical basis for parsing the structural environment in which law-related problems emerge and are addressed. From the array of conceptions about what it means to engage in systems thinking, this Article identifies four key tenets to this perspective: (1) every outcome is the product of some structure; (2) these structures are embedded within and connected to one another; (3) the structure producing an outcome can be discerned; and (4) these structures are resilient, but not fixed. This four-part framework provides a foundation for understanding systems as the contextual environment in which law is practiced. This Article defines surfacing and mapping as tools for engaging in systems thinking that, when incorporated into law school coursework, encourage students to address the presenting needs of a client in tandem with an assessment of the social and institutional systems that the client is a part of and affected by. Further, these tools promote reflection on the roles that attorneys play as both system participants and system architects. Learning objectives rooted in systems thinking promote understanding of organizational behavior, systemic functioning, and how these factors relate to effective advocacy. Systems thinking disrupts the tendency to screen out considerations of what is facilitated or hindered by the pressures and incentives that legal rules and social institutions create. Finally, this Article offers insights concerning the benefits of naming systems thinking as the theoretical core of efforts to recognize the broad social and political interdisciplinarities embedded in legal needs and tethered to the practice of law. Instruction in both the practice and paradigm of systems thinking equips law students to perceive and articulate these connections, as well as critique the role of attorneys in maintaining or disrupting them. Acknowledging systems thinking in legal education contributes to the evolving conception of what it means to “think like a lawyer”.