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Digital transformation (DT) is becoming essential for the competitiveness and sustainability of Small, Medium and Micro Enterprises (SMMEs), and yet many South African (SA) retailers have to overcome inhibitors that hinder them from digitally transforming. Therefore, this study explores these inhibitors to DT within the retail SMMEs sector in Eastern Cape and Western Cape provinces in South Africa using an exploratory multiple-case study design. Data from 23 in-depth semi-structured purposively sampled interviews were transcribed and thematically analysed on Atlas.ti 25 using the Braun and Clarke six-step framework to produce qualitative themes. The results reveal patterns of digital infrastructure constraints, a lack of digital literacy, financial and cost barriers, technical and operational challenges, psychological and attitudinal resistance, a lack of trust, safety concerns, and cyber risk, as well as business survival and strategic pressures, including the negative impact of the location where the business is located. Phased implementation, partnership with external stakeholders, and other strategic responses to these inhibitors requires targeted and strategic leadership and managerial interventions. This is the first study to combine Limits to Success Architype (LSA) and Adaptive Structuration (AST) in exploring the inhibitors to DT in retail SMMEs in South Africa.