With the disproportionately low number of minority and underprivileged students enrolled in advanced courses when compared to their more affluent peers, there has been a steady increase in the number of administrators employing open enrollment AP and IB programs in their high schools. There are multiple studies examining the effect of those open enrollment programs on student achievement and performance, but there is a noticeable gap in the extant literature utilizing hermeneutic phenomenology and portraiture to distill the essence of administrators’ lived experience within such an equity-minded initiative. This research study, anchored in the southeastern United States, sought to document and interpret the lived experience of leadership team members implementing both AP and IB open enrollment programs in their singular school site. To ascertain the administrators’ lived experience, the researcher collected data using the hermeneutic circle, Groenewald’s (2004) Phenomenological Research Design, Lawrence-Lightfoot and Davis’s (1997) portraiture, and a slight modification of Seidman’s (2006) in-depth phenomenological interview sequence. To ensure triangulation occurred in the study, the researcher included artifact analysis and memoing in conjunction with a modification of the in-depth phenomenological interview sequence. Data explication involved line-by-line coding to determine general and unique themes spanning all interviews and artifacts to give voice through portraits to administrators’ lived experience concurrently implementing an AP and IB open enrollment program in their high school.