Entrepreneurship is a critical driver of economic development in sub-Saharan Africa, yet businesses in Niger face a unique confluence of structural and institutional constraints. While enterprise development literature is extensive, comparative longitudinal analyses focusing on the evolution of these challenges and the institutional ecosystem are scarce. This study aims to systematically compare the predominant challenges confronting entrepreneurs with the evolving capacity of support institutions. It seeks to identify persistent gaps and assess whether institutional development has kept pace with entrepreneurial needs over a multi-decade period. A comparative case study design was employed, analysing secondary data from national surveys and institutional reports alongside primary data from semi-structured interviews with entrepreneurs and institutional representatives. Thematic and comparative analysis was used to identify trends and disjunctures. A persistent theme is the misalignment between institutional offerings and core entrepreneurial needs. While access to finance remains the most cited challenge (noted by over 70% of respondents), institutional support has disproportionately focused on basic business training. A significant finding is the growing importance of digital infrastructure as a barrier, which institutional programmes have been slow to address. The institutional landscape has evolved but remains reactive rather than anticipatory, failing to address the shifting, compound nature of entrepreneurial challenges. This misalignment stifles enterprise growth and limits poverty reduction potential. Support institutions should adopt a more integrated, technology-enabled service model. Policymakers must prioritise digital infrastructure development and foster public-private dialogues to better align support with real-time market challenges. entrepreneurship, institutional support, business environment, digital divide, Niger, Sahel This paper provides a novel longitudinal comparison of entrepreneurial challenges and institutional responses, introducing a diagnostic framework for assessing institutional alignment in fragile economic contexts.