This qualitative study explores teachers’ and administrators’ experiences with the educational strategy looping within middle-level settings. In contrast with the relative ease of identifying best practices, introducing and sustaining change in public school settings is challenging. National and state middle-level organizations suggest positive teacher-student relationships are critical for student success. Whereas some schools fail to deliberately provide structures to support the development of these relationships, other schools with structures in place meet with varying degrees of success with the interventions they implement. Within interviews and focus groups, the relevant obstacles teachers and administrators experience implementing middle-level looping programs are explored, including(a) what are the lived experiences of teachers and administrators involved in looping programs and (b) what conditions encourage the institutionalization of the strategy looping in the school settings in which it is introduced.