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Background Adherence to antiretroviral therapy (ART) is particularly important for patients with HIV. Prior research on ART adherence has focused primarily on behavioral interventions targeting patients and providers. No study has focused on the pharmacy refill experience as a potential target for improving adherence to HIV medicines. Informed by patients' experiences, this study aimed to assess patients' experiences with refilling their HIV medicines and to explore facilitators and barriers to refilling medicines on time. Methods We interviewed patients at three time points during their first year of care at an HIV clinic in Houston, TX. We analyzed interviews using directed and conventional content analysis. Results Analyses revealed individual, interpersonal, and system-level barriers that affect patients' ability to pick up their HIV medicines on time. Many patients perceived the refill process as being difficult. For some patients, picking up their HIV medicines each month triggered anxiety. Positive interactions with pharmacists and pharmacy staff, as well as clear and consistent messaging, played a key role in augmenting patients' refill experience. Self-efficacy, social support, and workarounds to resolve issues were also key facilitators. Many patients said changing ART-dispensing protocols from 30- to 90-day refills could mitigate the anxiety experienced with picking up HIV medicines and decrease opportunities for missing a refill. Conclusion Offering 90-day refills for HIV medicines may decrease anxiety concerning missed doses and improve medication adherence. Providing pharmacy staff with communication skills training is another strategy that may improve the patients' refill experience.