In watersheds across the American Pacific Northwest, changes in the cultural and regulatory landscape have increased pressure to restore and protect populations of anadromous fish. But restoration of anadromous fish populations constitutes a ‘wicked problem’, relentless in character, affecting diverse stakeholder groups, and defying ‘once and for all’ solutions (Weber & Khademian, 2008). Existing top-down institutions and adversarial processes appear to be poorly matched to resolve ‘wicked problems.’ In the Lower Crooked River watershed in Central Oregon, the management of the Bureau of Reclamation’s Crooked River Project is the preeminent factor influencing stream flow conditions for anadromous fish. Given the abundant opportunities for the use of litigation in systems with federal storage projects, and that legislation is typically required to make significant changes to the operation of federal storage projects, can collaboration offer a path to success, even when used alongside legislation? This research investigates the specific dynamics of the Lower Crooked River effort using a qualitative case study methodology. Semi-structured interviews with stakeholders in the Lower Crooked River effort suggest that although a collaborative approach has been useful in resolving fish passage and habitat restoration challenges, implementation of a suite of solutions embedded in the Crooked River Collaborative Water Security and Jobs Act of 2014 has been less successful. Following the model of collaborative governance developed by Ansell and Gash (2008), I attribute the challenges of implementation in the Crooked River case to the incongruence between the structure of collaborative process and the structure of legislative solutions. Delays in the legislative process and uncertainty surrounding the implementation of the legislation reduced the opportunity to develop elements of the collaborative process—trust, commitment, intermediate outcomes, face-to-face dialogue, and development of shared understanding and vision—that are important to achieving a successful outcome.