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BACKGROUND Community pharmacies are increasingly exploring the opportunities of digital transformation. This paper proposes a system based on computer vision to assist pharmacists in medication dispensing and check adherence to medication plans. OBJECTIVE The proposed solution uses artificial intelligence (AI), cloud, and mobile technology to support pharmacists in managing patient medication records, identifying possible medication errors when preparing pillboxes, and providing personalized information to end-users. METHODS Action design research was selected to design a technology readiness level 7 solution in a community pharmacy. RESULTS For theory, the project suggests design guidelines for AI-enabled medicine dispensing and evaluates success factors for community pharmacy digital transformation. For practice, this paper presents an example of low-cost intelligent medication dispensing suitable for nursing homes and patients with pill medication plans. AI-enabled systems can contribute to (1) prevent errors in filling pillbox compartments, (2) provide an additional cross-check in medication dispensing, and (3) identify medication adherence problems in more demanding scenarios of institutions with multiple patients. CONCLUSIONS Community pharmacies must have an active role in adopting artificial intelligence in their processes, creating their digital transformation strategy, not limiting their choices to the technology providers offer.