Rolling easements, legal mechanisms that allow coastal land-use flexibility while prohibiting shoreline armoring, are one tool in the climate change adaptation toolkit. Conceptually, rolling easements allow communities to balance the desire for coastal economic development and natural preservation while anticipating climate change impacts. However, the reality of their enforcement is fraught with legal hurdles. This paper aims to bridge a knowledge gap between planning journals and law reviews by connecting the distinct legal features of rolling easements to planning strategies. Specifically, this paper examines how five states have incorporated rolling easements into their Coastal Management Plans and then uses New York State as a case study to assess the feasibility of rolling easement implementation. By highlighting three different approaches New York could take towards integrating rolling easements, this paper seeks to facilitate a productive discussion about the opportunities and obstacles of how rolling easements could add to the field of coastal adaptation.