Background: Food-insecure (FIS) adolescents struggle in school and with health and mental health more often than food-secure (FS) adolescents. Rural communities experience important disparities in health, but little is known about rural FIS adolescents. This study aims to describe select characteristics of rural adolescents by food-security status. Methods: Baseline analysis using data from a randomized trial to increase school breakfast participation (SBP) in rural Minnesota high schools. Students completed a survey regarding food security, characteristics, and home and school environments. Schools provided academic data and staff measured height and weight. Food security was dichotomized as FS vs FIS. Bivariate analysis, multivariate linear/logistic regression, and testing for interaction of food security and sex were performed. Results: Food-insecure adolescents reported poorer health, less exercise, had lower grades, and higher SBP (p < 0.01). Food-insecure adolescents reported marginally fewer barriers (p = 0.06) and more benefits of breakfast (p = 0.05). All associations except reported benefits remained significant after adjustment. Interactions were identified with girls' grade point average and with boys' caloric and added sugar intake. Conclusions: Negative associations among food insecurity and positive youth development are identified in our sample. Policy and environmental strategies should address the complexities of these associations, including exploration of the role of school meals.