Making fresh fruits and vegetables (FFV) more widely available has been a prominent focus of healthy retail interventions and may have an important role in improving food access and diet quality at the population level. ‘Healthy retail’ interventions in corner/convenience stores (CS) are increasingly being adopted by public health practitioners to address the diet-related risk factors, improve food access at the community level, and change food retail environments. Private sector retailers are integral to the success of public health retailing interventions, making their perspectives and experiences critical. There is a particular need for greater evidence from retailers in settings where evaluations of these interventions have yielded null or mixed results. Through semi-structured interviews with 8 CS retailers (7 from urban settings and 1 from rural) in Ottawa, Ontario, Canada, this study aimed to describe experiences and critical factors regarding the feasibility and sustainability of a healthy CS program that was not sustained following the pilot testing phase, with a specific focus on the sale of FFV. Thematic analysis was used to analyze the interview data, which indicated that retailers faced two dominant challenges with selling FFV in CS: both relate to how these stores are embedded in the larger local and global food system. We join others in arguing that efforts and support for retail interventions aiming to increase the availability of FFV in CS need to address the structure and relations of the food system, as an upstream determinant of CS retailer interest and motivation.