Entry of large supermarkets and online retailers, and widespread adoption of digital technologies are threatening the business models of small retail convenient stores in India. Using a qualitative methodology and the Technology-Organization-Environment framework, this study, investigated the challenges faced by these small retail stores in the context of a deliberate governmental push towards digital payments and increasing competition from large supermarkets and online retailers. Perceived loss of control, costs of technologies, customers' low socio-economic background, suppliers influence, tax and security implications and bureaucracy and lack of trust on the regulatory and external environment are the challenges identified in the study. In addition, poor physical and digital infrastructure, inadequate access to and poor reliability of digital technologies, and the costs are constraining the adoption of digital technologies