The COVID-19 pandemic's border closures dealt a severe blow to Small Island States (SIS), revealing vulnerabilities in economic and food security due to heavy reliance on tourism. This crisis emphasized the necessity of robust food security systems to enhance economic resilience and safeguard livelihoods. Scant literature exists on specific challenges facing SIS food systems. This paper addresses these gaps, focusing on the Cucumis Anguria cucumber (comcomber chikito) in Aruba. Through participatory action research, consumer surveys, and expert interviews, significant constraints to food entrepreneurship are revealed, in areas such as innovation, technology adoption, entrepreneurial acumen, and risk mitigation. The study provides insights applicable to food systems in SIS, contributing to resilience-building efforts.