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Food sustainability is a significant global concern with drastic change required to mitigate complex social, environmental and economic issues like climate change and food security for an ever increasing population. In this paper, we investigate the roles that digital interactions might play in bringing about more sustainable food consumption practices. To inform this exercise, we set out to understand the place of food in people’s lives, their food practices, and the processes of transition, past and ongoing, that shape these. In particular, we contrast the journeys of ‘pioneers’ of sustainable food practice with more ‘mainstream’ consumers. We use our findings to highlight HCI design opportunities to support sustainable transitions in food practices, and promote wider participation in niche sustainable practices. We highlight the importance of designing to heighten, redirect, and sometimes rekindle the ‘meaningfulness’ of food and meals in people’s lives.