This research aims to reveal the effectiveness of academic supervision conducted by school principals, which consists of the planning, execution, evaluation, and followup, and any obstacles and the attempt by school principals to overcome them. This research uses an evaluation method with a descriptive quantitative approach. The research venues were state elementary schools across Yogyakarta, and the sample was 48 teachers selected based on proportional random sampling techniques. The data collection technique was a questionnaire. The data analysis technique was delivered using descriptive qualitative methods with percentages. The outcome of this research highlighted several issues. (1) The planning of academic supervision is very effective. (2) The execution of academic supervision is effective. (3) The evaluation of the execution of academic supervision is effective. (4) The follow-up of academic supervision is effective. (5) The main obstacle experienced by school principals is administrative duties, and hence the academic supervision is constantly delayed. Other obstacles are the principals' reluctance to supervise senior teachers, the lack of administrative support for teachers, and the willingness of teachers to be supervised. (6) The measures put in place to overcome these setbacks include rescheduling the supervision, pre-supervision teacher conferences, staff training and teachers' forums.