Adaptive management is challenging, even in the purest of circumstances. It requires experimentation and learning which is difficult to achieve in complex and constrained settings such as the U.S.-Mexico border region, particularly in the context of a changing and uncertain climate. This dissertation explores the limitations to adaptive management presented by both physical and psychological borders using the binational, bioregional, setting of the Tijuana River Watershed as a case study. It offers observations and evidence for opportunities to advance adaptive management through three studies: (1) an exploration of deficits in social capital to illuminate what underutilized social capital can be leveraged in adaptive management; (2) an examination of the process of collaborative community-based research as a method for improving tools for adaptive management; and (3) a characterization of the experiences of, and psychological impacts on, environmental professionals to suggest training and support to enhance their ability to adaptively manage in the Anthropocene.