This chapter explores the complex relationship between medication adherence, digital health, and patient-centred care (PCC), with a focus on chronic multimorbidity and polypharmacy. It begins by addressing the conceptual evolution of adherence and its determinants, followed by a discussion of how digital technologies can support person-centred approaches to improve therapeutic outcomes. The chapter presents Mobili®, an innovative portable automated dispenser, and outlines the design and implementation of the MobiMAd@PT project in Portugal. Drawing on international evidence and implementation science frameworks, it analyses the usability, effectiveness, and scalability of such interventions. Emphasis is placed on co-design, contextual adaptation, and integrated care models involving community pharmacies. The chapter concludes by outlining best practices for future digital adherence strategies, highlighting the importance of collaborative, user-driven approaches to enhance healthcare quality and sustainability.