The purpose of this multiple explanatory case study was to investigate the preparation of underserved school band programs for a Music Performance Assessment (MPA). Specifically, I examined racial, economic, and social inequalities, which are well documented in the research literature, and the related achievement gaps of underserved public school bands. Using Ladson-Billings' four pillars of educational debt, a replication approach highlighted four cases as a small sample of the success rate of Title I school bands scoring a Superior at an MPA contest. I compared how contextual issues impacted the four band directors at these schools in preparations for their bands' Music Performance Assessments. I used a critical realism paradigm to examine the disparities of secondary school bands within the context of financial means and hidden cultural expectations. Through this, I identified the academic, economic, moral, and sociological debts that high school band directors may encounter while teaching in an underserved school. These topics highlighted the band director perception on the MPA process, culturally relevant rehearsal strategies and musical selections, student-teacher relationships, and the preservice curriculum that prepares band directors to teach in a Title I school. Findings showed that each director's instructional design was heavily predicated on the socioemotional needs of their students while addressing financial challenges in promoting a positive rehearsal culture. Finally, I collected written and interview data that pointed to several themes and subsequent implications for future band director, university professors, administrators, and policymakers. My goal was to provide a comprehensive understanding of the challenges and strategies employed to prepare an MPA concert program for low-income schools, while addressing the longstanding inequalities in music education. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]