AbstractClimate change is threatening the status quo of agricultural production globally. Perennial cropping systems could be a useful strategy to adapt agriculture to a changing climate. Current and future perennial row crop systems have many and varied applications and these systems can respond differently than annuals to agricultural challenges resulting from climate change, such as shifting ranges of plant, pathogen, and animal species and more erratic weather patterns. To capitalize on attributes of perennial systems that assist in our ability to adapt to a changing world, it is important we fully consider the component parts of agroecosystems and their interactions, including species, genotype and genotypic variance, environment and environmental variance, adaptive management strategies, and farm socioeconomics. We review the current state of perennial grain and oilseed crops for integration into row crop agriculture and summarize the potential for current and future systems to support multiple environmental benefits and adaptation to climate change. We then propose a plant breeding strategy that incorporates the complexity of common domestication traits as they relate to future perennial crop improvement and adaptation and highlight digital technologies that can advance these goals. Evaluation of genetic gain during the development of new perennial crops and systems can be improved using research designs that span an environmental gradient that captures the forecasted shift in climate for a region, which we demonstrate by reanalyzing existing data. Successful development and deployment of perennial crops as a climate adaptation strategy depends on grower adoption, scalability, and sustainable modifications to markets and supply chains.