The entrepreneurial ecosystem in small island developing states presents unique structural challenges and opportunities. Understanding the specific constraints and strategic adaptations of enterprises within such contexts is critical for fostering sustainable economic development. This study aims to systematically identify and analyse the principal challenges faced by domestic enterprises and to map their strategic responses and perceived future prospects within the national business environment. A cross-sectional survey design was employed, administering a structured questionnaire to a stratified random sample of registered small and medium-sized enterprise owners and senior managers. Data were analysed using descriptive and inferential statistics. Access to finance was cited as a critical barrier by 78% of respondents, followed by bureaucratic inefficiencies and skilled labour shortages. A dominant strategic theme was the pursuit of digitalisation and market diversification to mitigate domestic market limitations. The findings indicate a resilient yet constrained entrepreneurial sector, where strategic innovation is often a necessity-driven response to systemic barriers rather than opportunity-driven growth. Policy interventions should prioritise streamlining regulatory processes, enhancing financial inclusion mechanisms, and fostering public-private partnerships for skills development. Enterprises are advised to formalise strategic planning and leverage regional trade agreements. entrepreneurship, small island developing states, business environment, strategic management, survey research, West Africa This paper provides the first comprehensive, longitudinal dataset on enterprise perceptions and strategies within this specific national context, offering a nuanced evidence base for targeted policy formulation.