As after-school programming has expanded in the U.S., there has been an increased empirical interest in understanding the impacts programs have on participating youth. Unfortunately, much of the research has focused on certain types of After School Programs (ASPs), primarily addressing tutoring and school-homework, and few have focused on underserved youth. This has resulted in a markedly limited understanding of non-academic ASPs, such as after-school music programs, and the underserved youth participating in them. This study addresses these gaps by exploring the experiences of seven successfully engaged underserved alumni who participated in Notes for Notes, an after-school music program. Building upon the findings from a prior study (Sheltzer & Consoli, 2019), the current study sought to gain a deeper understanding of how alumni experienced key program components, including meaningful relationships with staff, access to previously unavailable opportunities, program accessibility, physical and psychological safety, and freedom of expression. Analysis indicated a synergistic relationship between key elements of the program, staff characteristics, and alumni involvement, which resulted in a successful program experience as described by alumni. Specifically, alumni lauded several elements of the program such as the availability of free resources, the collaboration with the Boys & Girls club, and the safe and practical location. Affirming and supportive relationships with staff were considered crucial by alumni, especially in creating feelings of safety and acceptance. Additionally, engaged alumni described how they overcame barriers to accessibility, benefited from freedom of expression, took advantage of novel opportunities, and were motivated to “pay it forward.” A discussion of the implications of the findings, limitations of the study, and future directions is included.