Objectives: The objectives were to investigate the operational requirements for offering healthful vended reimbursable lunches to students and to identify barriers to implementation. Methods: A descriptive case study method was utilized to explore the operations of two school nutrition programs offering vended reimbursable lunches. Two school districts were selected based on availability and willingness to participate. A multiple case design followed a replication format, thus conclusions from each study site contributed to the whole. Structured and informal interviews, examination of documents and direct observations were used to gather data during a one-day site visit. Results: Two vending machines in a school in each participating district successfully vended reimbursable lunches to high school students. Three considerations were critical to this outcome: regulations, technology, and support. The ability to integrate point-of-sale software, cashless and vending machine technology, and school district electronic record keeping applications was the key element in implementing electronic compliance with USDA National School Lunch Program (NSLP) regulations. This interface of technology with regulations facilitated identification of legitimate reimbursable lunches, accurate provision of free and reduced price meals to eligible students, correct charges for full-pay meals, second meals and à la carte items, and maintaining confidentiality of meal eligibility category. The process entailed overcoming barriers and developing solutions to novel obstacles. All involved in the project stressed that it was possible only with the enthusiastic support of school nutrition program (SNP) and school district administrators, principals, and state agency administration overseeing the NSLP. Application to Child Nutrition Professionals: This qualitative study provided useful information for school nutrition program and school personnel, administrators, district financial personnel, and state agency professionals when considering innovative vending practices. The results offer guidance in implementing a vended reimbursable lunch that provides an additional menu option and the potential for increasing participation and revenue.