This chapter aims to shed light on institutional and contextual factors that may constitute constraints on entrepreneurship in the Cameroonian context generally and in the transport services sector in particular. For this purpose, it relies on documentary analysis of laws and regulations governing entrepreneurship in Cameroon and especially in the transport sector. A case study of three companies is used to validate or invalidate theoretical assumptions and the results of documentary analysis. Three main results emerge from this work. First, regulatory institutions governing entrepreneurship in Cameroon are sufficiently dynamic to promote entrepreneurship, even in the transport sector. Second, there are some contextual constraints that should be addressed to encourage investors to invest in the transport services sector. Third, rehabilitation of roads and creation of new roads should create new opportunities in the sector. Thus, institutional and contextual factors could impede or inspire entrepreneurship in Cameroon, and hence the Cameroonian government should pay attention to it.