Background: This study examined student and caregiver preference for school communication and explored the feasibility and acceptability of a digital tool to assist with communication about school meal program between schools and families. Methods: The study used qualitative methodology through youth focus groups and caregiver semi-structured phone interviews. The study was conducted in 4 high schools in a large, urban city. The phenomenon of interest included the exploration of preferences regarding communication around school meal programs and feasibility and acceptability of a digital tool for communication and promoting the ordering of healthful foods in the school environment. Interviews were transcribed, coded, and analyzed through NVivo qualitative software using thematic analysis approach to examine themes. Results: Forty-seven students (ages 14-21, grades 9-12) participated in 7 focus groups and 24 caregivers participated in semi-structured phone interviews. Three themes emerged around (1) communication preferences, (2) accessibility, and (3) extrinsic motivational factors for engagement in healthy eating behaviors. Conclusion: Results indicated that communication methods could potentially influence motivation and engagement in youth school meal participation.