Kenyan enterprises operate within a dynamic and often challenging economic environment. While the broader constraints on business growth in the region are acknowledged, a comprehensive, longitudinal analysis of the specific structural and operational hurdles faced by firms is lacking. This study aims to systematically identify, categorise, and analyse the predominant structural and operational challenges confronting enterprises. It seeks to assess the perceived severity of these issues and explore variations across different firm sizes and sectors. A stratified random sample of 450 registered enterprises was surveyed using a mixed-methods approach. The instrument combined Likert-scale questions to gauge challenge severity with open-ended items for contextual depth. Quantitative data were analysed using descriptive and inferential statistics, while thematic analysis was applied to qualitative responses. Access to affordable finance emerged as the most severe structural challenge, cited by 78% of respondents as a critical or very critical barrier. Operationally, a dominant theme was the inefficiency of public service delivery, which significantly increased administrative costs. Micro-enterprises reported disproportionately higher constraints related to regulatory compliance. The findings confirm that challenges are multifaceted but hierarchically structured, with financial access constituting a primary bottleneck. The operational burden of public service inefficiency exacerbates these structural constraints, particularly for smaller firms. Policymakers should prioritise de-risking mechanisms to stimulate lending to micro and small enterprises. Secondly, a targeted reform of business licensing and permit processes is urgently needed to reduce administrative friction. business constraints, enterprise survey, operational efficiency, structural barriers, financial access, East Africa This paper provides a novel, longitudinal dataset and a refined typology of business challenges, offering evidence for targeted policy intervention and serving as a benchmark for future comparative studies in similar economies.