The digital divide remains a persistent challenge for underserved small business sectors, particularly in rural and low-income urban communities where limited access to infrastructure, digital skills, and financial resources hampers the adoption of technology. This study examines the dynamics of technology acceptance and digital readiness within these underserved sectors, focusing on how socio-economic and organizational factors influence the adoption and effective use of digital tools. Grounded in the Technology Acceptance Model (TAM) and the Digital Readiness Framework, the research investigates perceived usefulness, ease of use, infrastructural barriers, and organizational culture as key determinants of digital uptake. Using a mixed-methods approach, the study combines survey data from 150 small business owners with qualitative insights from in-depth interviews across sectors including agriculture, retail, personal services, and informal trade. Results reveal that while awareness of digital tools is relatively high, actual usage remains low due to limited digital literacy, perceived complexity, and lack of technical support. Moreover, findings show that digital readiness is significantly influenced by prior exposure to digital solutions, leadership attitude toward innovation, and access to affordable internet connectivity. The research identifies three primary categories of readiness among small businesses: digitally proactive, digitally cautious, and digitally unaware. Tailored intervention strategies are recommended for each group to enhance adoption. These include targeted training programs, simplified onboarding for digital platforms, peer mentoring, and government-subsidized digital infrastructure. The paper concludes that improving technology acceptance and digital readiness in underserved small business sectors is crucial for enabling inclusive economic growth, reducing inequality, and enhancing competitiveness in a rapidly digitalizing global economy. It recommends that policymakers, development agencies, and technology providers collaborate to develop context-specific strategies that lower adoption barriers and build sustainable digital ecosystems for small enterprises.