Although it is true that government financial support for education is dwindling in many countries, most educational institutions in Uganda have failed to devise functional internal mechanisms to enable them to raise resources to continuously deliver quality education in quantity. Might the application of certain entrepreneurial strategies in educational management perhaps help to make a difference? What is educational entrepreneurship (EE)? How feasible is EE in a developing world education landscape like that of Uganda? Which challenges must EE surmount before it can envisage success? Using literature review methodology, this study attempted to find answers to such questions. Its aim was to delineate the EE domain and to highlight both its importance and feasibility in Uganda’s context. The study made two key discoveries; first, indeed EE is clouded in conceptual mishmash, hence need for more scholarly attention; second, however salvaging EE can be to struggling educational institutions, it is not without serious challenges – even apparent contradictions – hence preference for a “moderate risk” approach to entrepreneurship within educational institutions.