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This study examines the factors influencing online purchasing intention of customers in the retail industry, with particular reference to supermarkets in Sri Lanka’s Western Province. In the context of a rapidly evolving digital marketplace, understanding consumer behavior has become increasingly significant for both scholars and practitioners. The research investigates critical determinants such as trust, convenience, price perception, product variety, and technological adoption, highlighting their impact on consumer decision-making in online retailing. By focusing on supermarkets, which represent a vital component of the retail sector, the study provides a nuanced understanding of how customer attitudes and perceptions shape purchasing intentions. The findings contribute to the existing body of knowledge in consumer behavior, e-commerce, and retail management, while offering practical implications for supermarket operators, policymakers, and industry stakeholders seeking to enhance online engagement strategies. This work is intended as a resource for academics, researchers, students of business and management, and practitioners interested in consumer behavior and the development of digital retailing in emerging economies.