This study explores how socio-cultural complexities and institutional barriers affect the shopping experience of online groceries shoppers in Africa. Adopting a qualitative method with an interpretivist philosophy, 16 in-depth semi structured interviews were conducted with online groceries shoppers in Lagos, Nigeria. Findings reveal that while participants adopt online shopping due to convenience, product variety, and AI-powered decision-support devices, their engagement is constrained by digital mistrust, data insecurity, infrastructural limitations, and weak regulatory enforcement system. The theoretical contributions relate to the e-commerce and technology acceptance literature, and the managerial implications include insights for platform designers, retailers, and policymakers to enhance trust and digital inclusion. This knowledge will help to enhance the emerging markets’ digital retail landscape. Our paper also extends the current theorizing around institutional theory.