OBJECTIVE: We present the design and feasibility testing for the "Digital Drag and Drop Pillbox" (D-3 Pillbox), a skill-based educational approach that engages patients and providers, measures performance, and generates reports of medication management skills. METHODS: A single-cohort convenience sample of patients hospitalized with heart failure was taught pill management skills using a tablet-based D-3 Pillbox. Medication reconciliation was conducted, and aptitude, performance (% completed), accuracy (% correct), and feasibility were measured. RESULTS: The mean age of the sample (n = 25) was 59 (36-89) years, 50% were women, 62% were black, 46% were uninsured, 46% had seventh-grade education or lower, and 31% scored very low for health literacy. However, most reported that the D-3 Pillbox was easy to read (78%), easy to repeat-demonstrate (78%), and comfortable to use (tablet weight) (75%). Accurate medication recognition was achieved by discharge in 98%, but only 25% reported having a "good understanding of my responsibilities." CONCLUSIONS: The D-3 Pillbox is a feasible approach for teaching medication management skills and can be used across clinical settings to reinforce skills and medication list accuracy.