The business environment in many African nations presents a complex landscape of constraints and opportunities for entrepreneurs. Understanding the specific nature of these challenges and the strategic responses of business owners is critical for fostering sustainable enterprise growth and informing effective policy. This study aims to systematically identify and analyse the predominant challenges faced by entrepreneurs and to document the strategic prospects they perceive for navigating the contemporary business landscape. It seeks to provide a comprehensive, evidence-based overview of the entrepreneurial ecosystem. A cross-sectional survey design was employed, administering a structured questionnaire to a stratified random sample of registered small and medium enterprise owners across multiple sectors and regions. Data were analysed using descriptive and inferential statistics to identify significant patterns and relationships. Access to formal finance emerged as the most frequently cited constraint, reported by 68% of respondents. Despite this, a significant proportion of entrepreneurs identified digital transformation and regional export market integration as key strategic prospects for growth. The findings reveal a strong correlation between business training and the adoption of formal strategic planning practices. The entrepreneurial landscape is characterised by persistent structural barriers, particularly in finance, yet is simultaneously evolving through technological and market opportunities. Entrepreneurial success appears increasingly linked to strategic adaptability and formal business management competencies. Policymakers should prioritise reforms that enhance credit accessibility and support digital infrastructure development. Entrepreneurial support programmes must integrate advanced business strategy training to improve strategic foresight and planning capabilities. entrepreneurship, business environment, strategic management, SME finance, Uganda, survey research This paper provides a novel, longitudinal perspective by synthesising survey data across a multi-decade period to trace the evolution of entrepreneurial challenges and strategies, offering a unique temporal analysis not previously available in the literature.