This qualitative study explores various barriers to the customers’ usage intention of medicine delivery applications in Vietnam and describes customers’ attitudes and trust toward buying behavior. The positive and negative outcomes of such business activities are discovered by this study. The authors chose the study context of a chain of pharmacy, a prominent proxy in the peer-to-peer pharmacy business, and customers of pharmacy were interviewed to build a theoretical framework. The results of fourteen in-depth interviews identified six barriers: Usage Barrier, Risk Barrier, Value Barrier, Image Barrier, Complexity Barrier, and Consultation Services Barrier. The Brand Trust may also moderate the relationship between Distrust and Usage Intention. The data also indicated that a chain of pharmacies perceives three positive outcomes of their medicine delivery applications: past purchases-based consultation, direct chat with customers, business and customer analysis in detail resulting from the reviews of related pharmacy managers. The theoretical and practical implications are discussed in detail.