Originating as a primary art of fabric dyeing, Sri Lankan batik small and medium-sized enterprises (SMEs) have a high potential to position the country as an icon nation in the global marketplace. However, today, they face many challenges in developing their business due to poor technological adaptation, thus grappling with less competitiveness and remaining as a cottage industry. Grounded in the Technological-Organisational-Environmental (T-O-E) framework, this chapter explores creating a winning digital marketing strategy for Sri Lankan batik SMEs to be competitive and sustain their businesses. Using the multiple case study research design and the purposive sampling technique, data were collected by conducting semi-structured interviews with 12 entrepreneurs of Sri Lankan batik SMEs implementing digital marketing strategies. Findings stemming from thematic analysis reveal that digital marketing practices of batik SMEs vary, and 14 factors contribute to this variation. The 14 factors include computer anxiety, computer playfulness, computer experience, computer self-efficacy, perceived enjoyment, availability of financial resources, time scarcity, technical expertise, perceived benefits, ICT proficiency of employees, telecommunication infrastructure, availability of electricity facility, digital marketing complexity, and security and privacy concerns. These factors are further categorised as individual, organisational, and technological in nature. This qualitative study can be used as a grounding work extending practitioners’ understanding of the nature of these categories, which may lead to better insights into how to develop a winning digital marketing strategy for batik SMEs.