Complex prescribed medicine regimens require extensive self-management. Handling multiple pills can be confusing; using a pillbox organiser is a common strategy. A smart Medication Coach Intelligent Agent (MCIA) can support patients in handling medicine. The aim of this research was to evaluate the feasibility and acceptability of the MCIA. A prototype was tested with 15 participants, age 17–76, filled a pillbox according to prescription assisted by the MCIA implemented in a Microsoft HoloLens. A quantitative method using questionnaires was applied. Results showed that using the MCIA implemented in an AR-headset, to assist people with prescribed polypharmacy regimen in filling a pillbox, was feasible and acceptable. There was a difference related to age regarding people’s willingness to use an AR-headset for medication self-management. People older than 65 felt less comfortable using the technology and were also more hesitant to use the technology than those under 65.