This policy report proposes that community gardens have the potential to be a reliable basket that adds to Singapore’s food supplies, focusing on leafy vegetables. This is given the availability of usable spaces for growing crops on public and private estates, rooftops, schools, organisations/institutional facilities, interim land, and industrial spaces. However, regulatory requirements for farmers to sell their produce are currently tailored for commercial farm establishments and thus conceivably too complex for individual community farmers. Moreover, productivity levels are low given community gardeners’ limited time and investments in growing food. This report highlights how digital technologies can help transform food farming to address community farmers’ “pain points”, making it a more viable enterprise. It concludes with two recommendations: i) to encourage the formation of organised community clusters to navigate the complex regulatory requirements for selling food, and ii) to conduct digital-readiness assessments on community farmers’ attitudes towards digital technology adoption.