The study was assessing challenges facing procuring entities in complying with Procurement regulations. The study adopted a case study design that allowed collection of data at one point in time. Structured questionnaires were administrated to a sample of 50 respondents comprising Workers from Kisarawe District Council specifically from procurement department, other member from user departments were also included. The data were analysed by using different computer software such as MS Excel and Statistical Package for Social Sciences (SPSS). The analyses of data were largely descriptive involving computation of frequencies and percentages. The study results show that overall compliance level on average is 43.8% which is not even greater than a half of total compliance, some area had highest while others had lowest compliance level, and advertisement to bid was highest element of compliance while publication of award was the lowest scored 2%. It was further revealed that there are number of challenges that hinder effective compliance of the procurement regulations; among the challenges are corruption in public procurement, interference from interest group specifically politicians, lack of professionalism, lack of enough skilled personnel, legal environment, market condition, lack of training opportunities and lack of training opportunities Moreover, the finding of this study revealed that staffing of PMU was one of the area which had problem in PPRA audit report and this can be seen from analysis of challenges, therefore skilled procurement personnel has been perceived as the root cause of non-compliance at Kisarawe District, it has been noted that inadequate skilled personnel may lead to lack of professionalism, lack of ability to interpret legal environment of contracts etc. Finally, the study shows that compliance of procurement regulations depends much on two important elements, skilled personnel and integrity/ethics of conducts, so to enhance these elements training remain critical in enhancing compliance.