Evidence suggests that simple text messaging interventions may not suffice to improve ART adherence among youth in low-resource settings. To address this shortcoming, we developed an intervention that shared weekly real-time adherence feedback to youth in Uganda using short message services (SMS), based on information tracked by an electronic device (Wisepill). We present results from 7 formative and 6 exit focus groups (FGs) in Mulago and Entebbe, Uganda with youth ages 15–24, providers, and Community Advisory Board members. Participants consistently conveyed positive impressions of Wisepill, noting that it helped store their medications, facilitated travel, served as a reminder, and motivated adherence. Participants raised phone-related issues before the study; most were addressed but some remained (e.g., limited network access, electricity for powering phones). Further, they highlighted the importance of carefully crafting text messages (e.g., use slang rather than potentially stigmatizing words) and viewed personalizing messages favorably but were divided on the desirability of including their name in study-related texts. Exit FGs confirmed that sharing group adherence levels with participants tapped into the competitive spirit common among youth. Our results suggest future mobile technology-based interventions can be improved by providing messages that go beyond simple reminders to provide individual and group-level adherence feedback.