The increased use of online pharmacy services in the midst of the COVID-19 pandemic provides an important backdrop against which to examine the role of neurocognitive functions in health-related Internet navigation skills among persons with chronic medical conditions, such as HIV disease. Prospective memory (PM) is reliably impaired in HIV disease and is related to laboratory-based measures of medication management capacity in other populations. This study examined whether PM shows veridicality in relationship to online pharmacy navigation skills in persons with HIV disease. Participants included 98 persons with HIV disease age 50 and older who completed the Cambridge Prospective Memory Test (CAMPROMPT) and the Medication-Management Test-Revised (MMT-R) as part of a neuropsychological study. Participants also completed the Test of Online Pharmacy Skills (TOPS), which required them to navigate a simulated, experimenter-controlled online pharmacy to perform several naturalistic tasks (e.g., refill an existing prescription). Lower PM had medium associations with poorer MMT-R and TOPS accuracy scores that were not better explained by other neurocognitive functions. The association between PM and TOPS accuracy was driven by errors of omission and did not vary meaningfully based on whether the intention was cued by time or an event. These data suggest that PM cue detection processes show veridicality with online pharmacy navigation skills. Future studies might examine the benefits of PM-based strategies (e.g., salient prompts) in supporting online health navigation skills in populations that experience clinically impactful PM failures.