The literature on entrepreneurship in developing economies often presents a dualistic tension between structural constraints and individual agency. Understanding how entrepreneurs perceive and navigate this interplay is critical for effective business support, yet comprehensive survey data capturing this dynamic over an extended period are scarce. This study aims to systematically analyse the perceived key issues facing businesses, specifically examining the relationship between external structural barriers and internal entrepreneurial actions. It seeks to identify the most salient constraints and the strategic responses employed to mitigate them. A longitudinal, structured survey was administered to a stratified random sample of registered small and medium-sized enterprise owners and managers. The instrument combined Likert-scale assessments of constraint severity with open-ended questions on strategic adaptations. Data were analysed using descriptive statistics and thematic analysis. Infrastructure deficits, particularly unreliable electricity and transport networks, were cited as the most severe constraint by 78% of respondents. A key theme emerging from the qualitative data was 'constrained agency', where entrepreneurs developed highly localised, informal coping strategies—such as collective generator sharing—to bypass systemic failures, rather than being paralysed by them. The findings challenge narratives of entrepreneurial passivity in the face of structural impediments, demonstrating a pattern of innovative, though often costly, micro-level adaptations. This suggests that business diagnostics must account for both the objective severity of constraints and the subjective, agentic navigation of them. Policymakers and development agencies should design support mechanisms that recognise and formalise effective informal coping strategies. Business advisory services must shift from generic best-practice models to context-responsive frameworks that build upon existing entrepreneurial ingenuity. entrepreneurial agency, structural constraints, business environment, survey, Uganda, coping strategies This paper provides a novel, longitudinal dataset and analytical framework that synthesises structural and agentic perspectives, offering a more nuanced diagnostic tool for researchers and practitioners in behavioural business studies.