Due to the entry of huge supermarket chains and internet merchants, the traditional business model of small retail convenience businesses in India is coming under growing pressure. The digitalization of small retail establishments was examined in this study utilizing a qualitative technique and the Technology-OrganizationEnvironment framework as the theoretical underpinning. Our analysis indicated a high reliance on low value cash and credit-based transactions and low levels of adoption of digital technologies for managing supply-side and customers-side activities. Small retail establishments' capacity to go digital is being hampered by ineffective procedures, shoddy physical infrastructure, inadequate access to and unreliability of digital technologies, and costs. The current digital era is characterized by a significant amount of continuing, ICT-led technological progress and ever-increasing rivalry. New and late entrants are concerned about their future in the face of fierce rivalry, while established enterprises and early entrants are concerned about rising competition and shrinking profit margins. Digital disruption has reduced the lifecycles of company models, making business model innovation essential to attaining financial success. Small retailers' inability to comprehend the changes and resources needed to meet the challenges is evidenced by their expressed ambiguity and inherent contradictions regarding the advantages of transparency, perceived sense of control, tax implications, and mistrust of external regulations in the context of digital commerce.