The enactment of No Child Left Behind's (NCLB) Supplemental Educational Services (SES) provision shifted new attention to the ability of afterschool programs to increase students' achievement levels and help close the pervasive achievement gap between Students of Color and their white counterparts. Though studies of supplemental education programs in general have shown their potential to successfully augment traditional classroom instruction, reports thus far on indicate that states, districts, providers, and families have faced numerous challenges in the execution of the SES model. The scant research that exists on SES primarily has focused on national, state, and district-level investigations of implementation. With the upcoming reauthorization of NCLB, information in needed on the ground-level implementation of SES, and the lived experiences of participants within SES Provider organizations, particularly those in urban areas that face significant social and economic challenges. This purpose of this study was to include the voices of SES program participants in the dialogue surrounding the provision's redesign and to understand their individual perceptions of the opportunities and challenges of involvement within one SES Provider program in the District of Columbia. Participant stories revealed that, despite some challenges, the program of study was beneficial and fostered the academic, social, and personal development of student participants, including increases in grades, test scores, and attendance, as well as in self-esteem and confidence. Tutors and staff reported experiencing personal growth and development. Participant narratives also uncovered a number of challenges that exist in the implementation of SES policy within the District of Columbia Public School System (DCPS), including issues with timing, communication, and district expectations. Participant experiences within the DCPS and subsequent policy recommendations may help to inform SES policy moving forward to aid in the development of policy that truly works to the benefit of the individuals it was intended to serve.