Educational innovations continue to improve schools' abilities to implement up-to-date, effective, efficient evidence-based practices. Across education, it is important to understand the implementation and contextual elements that are critical to educator acceptability, feasibility, and usability. This preliminary qualitative study seeks to better understand practical and lived challenges to Tier 2 social, emotional, behavioral implementation, specifically the systematic Tier 2 Identification and Intervention training and implementation framework and what barriers and facilitators assist trainers and practitioners with implementation. Across eight participants in eight schools, four primary themes were identified: (1) buy-in, (2) failures and misunderstandings, (3) teamwork, and (4) perceptions of framework affordances and requirements. We present details on these findings and the practical implications for educators, administrators, and school psychologists.