Individuals who are disadvantaged by low-income and/ or minority status face a number of barriers to experiencing optimal health and eating well. Twenty Aboriginal and 29 non-Aboriginal participants (N = 49) from Ottawa, Canada took part in a cross-sectional, mixed methods study and completed one questionnaire and single in-depth interview that verified: 1) food security status and household eating habits, 2) fruit and vegetable purchase and consumption, and 3) knowledge about or participation in the Good Food Box [GFB] Program. Ottawa GFB staff (n = 5), site coordinators (n = 6) and steering committee members (n = 3) took part in separate discussion groups to identify challenges and strengths related to program coordination, management and delivery. Within an ecological framework, qualitative data is discussed using a social phenomenological and thematic approach. Using χ2 analyses, results suggest a medium effect size and association between food security status and Aboriginal identity (χ2(1) = 8.04, p < 0.01; φ = 0.4) and satisfaction with how stores meet household food needs and gender (χ2(1) = 5.86, p < 0.05; φ = 0.36). A relationship between participation in the GFB Program and food security status (χ2(1) = 11.13, p < 0.01; φ = 0.48) is also shown where estimates suggest that GFB customers are 9.9 times more likely to be food secure compared to non-affiliates. ANOVA results and post-hoc tests demonstrate a significant mean difference in frequency of fruit consumption between GFB customers and non-program users (F(2, 46) = 11.29, p = 0.00) where 29.6% of the variance (ω2 = 0.296) is explained by program participation. Results-based and community-driven recommendations to improve access to healthy food, food security and the GFB Program are discussed as shared responsibilities between different levels of government across sectors and the community since these are public and social health issues, determinants of health and economic concerns. Implications of findings are also discussed.