Adaptive management has been defined and redefined in the context of natural resource management, yet there are few examples of its successful application in ecological restoration. Although the 2009 Delta Reform Act now legally requires adaptive management for all restoration efforts in the Sacramento-San Joaquin Delta, in California, USA, projects in this region still encounter problems with implementation. We used a comparative case study analysis to examine adaptive management planning and implementation both in and around the Delta, assessing not only why adaptive management is not yet well implemented, but also what changes can be made to facilitate the adaptive management approach without sacrificing scientific rigor. Adaptive management seems to be directly and indirectly affected by a variety of challenges and convoluted by ambiguity in both planning documents and practitioner’s interpretations of the concept. Addressing these challenges and ambiguities at the project level may facilitate the adaptive management process and help make it more accessible to practitioners.