The purpose of this study is to examine the impact of educational software characteristics on software performance through the mediating role of user acceptance. Our approach allows for a deeper understanding of the factors that contribute to the effectiveness of educational software by bridging the fields of educational technology, psychology, and human–computer interaction, offering a holistic perspective on software adoption and performance. This study is based on a sample collected from public and private education institutes in Northern Greece and on data obtained from 236 users. The statistical method employed is structural equation models (SEMs), via SPSS—AMOS estimation. The findings of this study suggest that user acceptance and performance appraisal are exceptionally interrelated in regard to educational applications. The study argues that user acceptance is positively related to the performance of educational software and constitutes the nested epicenter mediating construct in the educational software characteristics. Additional findings, such as computer-familiar users and users from the field of choral music, are positively related to the performance of the educational software. Our conclusions help in understanding the psychological and behavioral aspects of technology adoption in the educational setting. Findings are discussed in terms of their practical usefulness in education and further research.