The business environment in many African nations is characterised by significant structural and operational challenges that impede enterprise growth and economic development. Understanding the specific nature and persistence of these constraints is critical for formulating effective policy and support mechanisms. This diagnostic survey aims to systematically identify and analyse the predominant challenges and latent prospects faced by businesses within a specific national context. It seeks to assess the evolution of these factors over a significant period and evaluate their impact on enterprise sustainability and expansion. A comprehensive, longitudinal survey methodology was employed, synthesising data from a stratified sample of formal and informal enterprises. The approach combined quantitative analysis of business climate indicators with qualitative thematic analysis of owner-manager narratives to provide a holistic diagnostic. The analysis reveals that access to finance remains the most pervasive constraint, cited by over 70% of surveyed enterprises as a critical barrier to growth. A significant thematic finding is the increasing prominence of digital adaptation as both a challenge and a key prospective avenue for competitiveness. The business landscape, while fraught with enduring systemic challenges, is undergoing a gradual transformation. Prospects for improvement are intrinsically linked to targeted interventions in financial infrastructure and technological adoption. Policymakers should prioritise the development of inclusive financial products beyond traditional microcredit. Furthermore, fostering public-private partnerships to enhance digital literacy and infrastructure is essential for improving business resilience. Business environment, diagnostic survey, enterprise constraints, access to finance, digital adaptation, business climate, Uganda. This paper provides a novel, longitudinal dataset and diagnostic framework that tracks the evolution of business environment constraints, offering a evidence-based foundation for prioritising policy and development finance interventions.