This article focuses on the debates among resilience, sustainability, adaptation, and transformation concepts. The conceptualization and application of sustainability and resilience thinking in the human-environmental interactions, social-ecological systems, and global environmental change literature remain dominant, which provide a common interdisciplinary and policy language where research in socio-environmental systems can converge. Yet, the lack of clarity and multiplicity among and between these concepts and paradigms allows them to continue to be widely adopted in different sectors of society. Drawing on five case studies from different geographical locations, these diverse applications of resilience, sustainability, adaptation, and transformation are explored from disciplinary and interdisciplinary perspectives. The diversity in the operationalization and use of the concepts and paradigms can result in applications that undermine goals of sustainability or resilience when a particular resource is prioritized over others or is applied in a way that results in inequitable outcomes. Findings from the cases reinforce the importance of being explicit about the spatial, temporal, and institutional boundaries drawn because proposed solutions will vary in their effectiveness if attention to scale, stressors, worldviews, and actors are not addressed holistically. We suggest the ongoing adoption of sustainability, resilience, adaptation, and transformation requires clear and explicit definitions, that draw from decolonized methodologies, goals, in-depth analysis of potential unintended consequences, and situated understanding of how these concepts and the associated paradigms are embedded in particular contexts.