Personalized drug delivery systems (PDDS), implying the patient-tailored dose, dosage form, frequency of administration and drug release kinetics, and digital health platforms for diagnosis and treatment monitoring, patient adherence, and traceability of drug products, are emerging scientific areas. Both fields are advancing at a fast pace. However, despite the strong complementary nature of these disciplines, there are only a few successful examples of merging these areas. Therefore, it is important and timely to combine PDDS with an increasing number of high-end digital health solutions to create an interactive feedback loop between the actual needs of each patient and the drug products. This review provides an overview of advanced design solutions for new products such as interactive personalized treatment that would interconnect the pharmaceutical and digital worlds. Furthermore, we discuss the recent advancements in the pharmaceutical supply chain (PSC) management and related limitations of the current mass production model. We summarize the current state of the art and envision future directions and potential development areas.