The present study focuses on the exploration of the perceptions and experiences of school administrators (principals and vice-principals) and teachers regarding school improvement and influencing contextual factors. Designed as case study research, this study utilized data gathered from school principals, vice-principals, and teachers from various school levels in the fall semester of 2019-2020 academic year. The researcher collected data in a graduate-level course offered in a master’s program without a thesis at a large state university in Southeastern Turkey through course assignments. Delving into school improvement perceptions and experiences from the eyes of three different groups of practitioners offered significant insights into contextual factors, namely hindrances to and enablers of school improvement, along with the steps to be taken at the praxis level and certain external factors. The results of the research might indicate that both issues related to the human side of school improvement such as the behaviors, practices, and attitudes of school staff, students and parents and the structural side like physical characteristics, budget, education system, and socioeconomic status of school environment have impacts on school improvement. These factors are likely to govern school improvement efforts and outcomes.