Smallholder farmers are key actors in addressing the food and nutrition insecurity challenges facing the Caribbean Community (CARICOM), while also minimizing the ecological footprint of food production systems. However, fostering innovation in the region's smallholder farming systems will require more decentralized, adaptive, and heterogeneous institutional structures and approaches than presently exist. In this paper, we review the conditions that have been undermining sustainable food and nutrition security in the Caribbean, focusing on issues of history, economy, and innovation. Building on this discussion, we then argue for a different approach to agricultural development in the Small Island Developing States of the CAR-ICOM that draws primarily on socioecological resilience and agricultural innovation systems frameworks. Research needs are subsequently identified, including the need to better understand how social capital can facilitate adaptive capacity in diverse smallholder farming contexts; how formal and informal institutions interact in domestic agriculture and food systems to affect collaboration, co-learning, and collective action; how social actors might better play bridging and linking roles that can support mutual learning, collaboration, and reciprocal knowledge flows; and the reasons underlying past innovation failures and successes to facilitate organizational learning.