South Africa's Central Chronic Medicine Dispensing and Distribution (CCMDD) program provides community-based medication delivery for clinically stable people with HIV (PWH) on antiretroviral therapy (ART). To evaluate CCMDD implementation, we conducted semi-structured interviews with 60 PWH enrolled in CCMDD for at least 12 months. In a directed content analysis based on the Practical, Robust Implementation and Sustainability Model (PRISM) implementation science framework, key themes were compared with qualitative data collected from PWH enrolling in CCMDD at an earlier time-point. Results indicated consistently positive views of CCMDD, primarily attributed to convenient and smooth medication pick-up. At the later (vs. earlier) time-point, participants discussed less clinic crowding, mentioned few medication errors, and noted improved communication around refills. Community HIV stigma was a persistent challenge, as was nurses' judgmental communication style. To ensure CCMDD's success, continued focus is needed on decreasing HIV stigma beyond the clinic context and improving provider-patient relationships.