In this article, I reflect on the implication of the urban land tenure systems of the three political regimes of Ethiopia on the objective element of land tenure security of urban landholders, particularly, permit holders. The objective element of land tenure security can be assessed in terms of clarity and breadth, duration, assurance, and enforceability of land rights. On these foundations, I argue that the objective element of tenure security of urban landholders in Ethiopia has been reduced with each subsequent regime. The Imperial regime’s urban land tenure system affected the objective land tenure security of urban landholders in terms of enforceability of land rights—particularly limiting the right to appeal to a presumably independent court of law with regard to the amount of compensation awarded for the loss of land rights through expropriation. The Derg regime’s urban land tenure system, on the other hand, had narrowed the breadth of land rights to possessory right; it introduced other grounds in addition to expropriation, by which a landholder could lose his land rights, it adopted a vague and broad understanding of “public purpose” for expropriation, and it introduced a compensation scheme that left a landholder compensated inadequately; and it totally prohibited bringing a legal action in presumably an independent court of law against the government. Even more, the post-1991 urban land tenure system has perpetuated the objective land tenure insecurity of permit holders by making the land rights unclear until the enactment of regulation; and to be valid for a definite period of time by mandatorily demanding its conversion to lease system.