This project report investigates the strategic challenges encountered by Small and Medium Enterprises (SMEs) within the cottage industry in Tobago. The research begins with an introduction outlining the background, problem definition, rationale, research question, aims, and objectives. Chapter 2 provides a literature review, defining SMEs, discussing their contribution to economic development, and analyzing the specific strategic challenges faced by the cottage industry in Tobago, such as lack of credit, high transportation costs, old machinery, insufficient skilled labor, undeveloped markets, and scattered distribution. The chapter also proposes solutions to these challenges, including developing market identity, product promotion, establishing market infrastructure, e-marketing, and improving transportation linkages. Chapter 3 details the research design and methodology, including the research paradigm, methodology, data collection methods (questionnaires and interviews), sampling method, data analysis techniques, ethical considerations, limitations, and a research timetable and project plan. The study uses a positivistic paradigm and a quantitative data analysis approach to examine the challenges and propose potential solutions for SME development in Tobago's cottage industry.