Digital Pills are a developing technology with application in a variety of medical conditions. This paper reports on interviews from a crossover clinical trial in which participants used both a novel digital pill system (ID-Capsule) and an electronic pill dispenser (Wisepill). Interviews explored user experiences, acceptability, and willingness to use both products. Data for each period of use is reported, and experiences about the two products are compared. The electronic pill dispenser was considered easy to use and convenient. The size of the pill dispenser was cited as both a facilitator and barrier to ongoing pill use. The ID-Capsule digital pill system was considered a facilitator of adherence for many users, and most found that knowing that their adherence was being monitored encouraged adherence. Using the accompanying ID-Capsule app to track days on which pills were missed was helpful. Barriers included needing to use and charge the digital pill reader. These qualitative findings provide relevant technology evaluation data for use in future iterations of this digital pill and adherence system.