The growth of digital commerce and changing consumer behavior have increased pressure on traditional food-based Micro, Small, and Medium Enterprises (MSMEs) to adapt their marketing practices. However, evidence on how digital marketing transformation develops at the firm level remains limited, particularly in semi-urban and rural contexts. This study examines how cassava chips MSMEs in Deli Serdang Regency implement digital marketing, perceive its marketing-related outcomes, and experience the constraints and support mechanisms shaping the transformation process. A qualitative multiple-case study was conducted involving four cassava chips MSMEs, one local government officer, and one digital marketing facilitator. Data were collected through in-depth interviews, non-participant observations, and document analysis, and were analyzed using reflexive thematic analysis. The findings show that MSMEs use social media, online marketplaces, WhatsApp Business, and basic visual content to support promotion, customer communication, and transactions. These practices were associated with perceived improvements in market reach, customer responsiveness, and brand visibility. Nevertheless, adoption remained fragmented, operational, and weakly integrated with strategic marketing planning. Limited digital literacy, human resources, time, infrastructure, and follow-up support constrained capability development. This study concludes that digital marketing transformation among traditional food MSMEs is an iterative capability-building process rather than merely technology adoption. Sustainable transformation therefore requires long-term mentoring, simplified strategic guidance, and coordinated institutional support that align digital tools with business objectives.