Micro, Small, and Medium Enterprises (MSMEs) are widely recognized for their vital contribution to sustainableand inclusive development, particularly through their role in employment generation and national economicgrowth. In the context of a rapidly evolving digital economy, the sustained growth and resilience of MSMEsincreasingly depend on their capacity to adopt and integrate digital technologies. This study examines thedigitalization challenges confronted by small enterprises. Using a qualitative research design, six participantswere purposively selected based on asset classification and level of digital technology adoption. Thematic analysisof the interview data revealed five significant challenges: (1) the persistence of manual processes and hybridoperational practices; (2) workforce adaptability gap; (3) infrastructure and digital system constraints; (4) financialand trust barriers in digital systems; and (5) enablers of digital readiness. The findings highlight that while smallenterprises recognize the potential benefits of digitalization, structural constraints and capacity limitationscontinue to hinder full adoption. The study emphasizes the importance of targeted capacity-building programs,affordable digital solutions, and supportive policy interventions in promoting the inclusive and sustainabledigitalization among small enterprises.