Reports on one-to-one (1:1) technology initiatives emphasize overall favorable results; however, comprehensive multiyear studies looked at understate the progressive experiences of teachers and students. A small body of research suggested the second year of 1:1 technology programs manifested difficulties and struggles which significantly contrasted with the first year of implementation. The purpose of this case study was to discover any negative experiences of participants during the second year of a 1:1 technology initiative, and understand how those experiences influenced the success and sustainability of the program. Data suggest that participants felt the goals of the initiative were not being met, evidenced by a significant decrease in desired teaching and learning outcomes.