The Sacramento-San Joaquin Delta is in a state of inevitable transition. Physical and financial pressures are likely to transform parts of the Delta into open water within the next 100 years. Because flooded islands have different habitat, water quality, and hydrodynamic implications depending on location, depth, orientation, and other physical factors, the state may decide to intentionally flood one or more Delta islands in an effort to better manage the Delta’s ecosystem and valuable water supplies. This paper outlines three sets of near term actions the state would have to take to begin transitioning towards intentional island flooding, and discusses legal and political challenges to those actions. Several key findings include the following: (1) amendments to California’s water code and revisions to the Delta Land Use and Resource Management Plan may help the state ensure the legal authority to differentiate levee policies within the Delta; (2) permits for a first, experimental flooded island will likely require the State Water Resources Control Board to revise the Delta Water Quality Control Plan to allow for more short-term flexibility and deal with conflicting ecosystem and water supply uses; and (3) the state may want to prepare mitigation plans for private landowners on neighboring islands whose levees could face new threats of erosion and/or seepage from a nearby flooded island in order to avoid inverse condemnation lawsuits. If the state decides to shift its levee policies in the Delta, serious consideration will need to be given these and additional common, regulatory, statutory, and constitutional laws.