Property reparation programs undertaken in Central and Eastern Europe after the fall of the communist regimes fail to fulfill ‘the promises of the rule of law’. Reparation schemes do not have an exclusively reparative nature, moreover, reparation was deliberately linked with structural reform, and due to this duality, the scheme features a mixed distributive-reparative character. This resulted in two troublesome aspects: on one hand, there is no evidence of a compelling argument, which justifies the mitigation of past property deprivations at large. On the other hand, it can not be satisfactorily demonstrated why property-related injustices enjoy a privileged status when it comes to reparations, in comparison to other types of losses. Further, bearing in mind the Hayekian objection towards distributive justice, even those who had been placed in an equal situation—i.e. all suffered past property injustices—are not offered an objectively equal opportunity to claim redress. Due to the fact that the schemes addressed reparations—at least in part—from a distributive perspective (which resulted in an attempt to create a substantive equality between victims), the result that they achieved was objective inequality, as everyone was entitled to reparation between the same limitations, while everyone suffered losses of different extent. These differences in treatment between various former owners are mostly arbitrary, and in certain cases deliberately introduced so as to produce inequalities, and thereby meet the Hayekian concerns as far as they produce results that conflict with the idea of the rule of law. The analyzed provisions of the reparation schemes lead in practice to the creation of winners and losers of reparations, to a breach of the idea of formal equality before the law. In the conditions in which reparation schemes fall short from a thick conception of the rule of law (justice, rights or objective equality) it worth investigating, whether requirements of a thin reading-focusing on foreseability, clarity and consistency—are still met by post-communist property redistribution. Unfortunately at least under three aspects—valuation, time limits and probation—the reparation schemes’ provisions are not beyond criticism. The complexity of tasks that transition societies had to face is obvious and uncontested. Transitional law, according to Teitel, is a sui generis paradigm, a vehicle of social, political and ideological transformation. The amendments to the rule of law ideal, justifiable in the context of transition can go as far as—for example—to allow governments to decide upon the concrete form of the reparation, the type of wrongs it want to address, the period in time intended to be covered. But they may not create winners and losers; they may not distinguish between those placed in the same situation.