Crop rotations have formed a fundamental component of agricultural systems for millennia. Improved decision support systems for crop rotations hold great potential for improving soils and agricultural sustainability. New opportunities exist to gather and collect on farm data at unprecedented temporal and spatial resolution and frequency, heralding an age of personalized decision support tools for which learn and provide adaptive recommendations for multiple sustainability indicators, based on time-varying constraints, and real time data on climate, markets, and pests. At the heart of this new development is the requirement for better human centered design, improved efforts to understand of how farmers think and feel and a sharper alignment of interests between technologists and farming communities to improve access, and to facilitate long-term agricultural transformation into the future.