The barriers and enablers of enhanced crop diversification were investigated by LEAF (Linking Environment And Farming) through workshops and case studies undertaken as part of three separate collaborative projects in 2019–2020. The main enablers identified were the perceived benefits of soil health and crop protection. The main barriers highlighted were the cost and availability of suitable machinery for drilling and harvesting, as well as grain separation for certain markets. Increasing the uptake of intercropping and enhanced crop diversification on a larger scale in the UK requires effective knowledge exchange to highlight opportunities and benefits and help overcome practical barriers.