A pilot study evaluated the integration of PortionSize Ed (PSEd), a dietary assessment app, into the Hawaii Food and Lifeskills for Youth (HI-FLY) program, which is part of the Supplemental Nutrition Assistance Program Education. The study focused on adolescents in grades 6-8, assessing the feasibility, acceptability, and early effects of this technology in enhancing diet quality. Out of 50 students, 42 (84%) enrolled, with minimal attrition at 2.4%. The participants were mostly female (49%) and predominantly Native Hawaiian or Pacific Islander (85%). User satisfaction was high, with average survey scores above the midpoint. While no significant changes in overall diet quality were observed, the use of PSEd led to reported improvements in sugary drink consumption and increased use of nutrition labels among participants. The findings suggest that combining mobile health technology with community-based nutrition education is feasible and can encourage positive dietary behavior changes among youth in Hawaii.