Market value is the most common compensation basis for expropriation of both private and customary property rights. Private property rights are generally exchangeable while customary property rights are conceptually not as exchangeable. It is hence critical to analyse the applicability of current compensation theories, which are founded on private property rights, to different property rights and in different social settings. By using existing literature and empirical evidence from Africa and other countries where customary property rights dominate, this paper undertakes a theoretical analysis of the applicability of existing compensation theories and the methodologies used to achieve the desired compensation goals. The analysis concludes that whilst current compensation theories are broadly applicable to customary property rights as they aim to protect property rights and prevent expropriatees from impoverishment, various ontological and methodological factors limit the realisation of these goals in settings dominated by customary properties. Such factors include ontology and dominance of customary property rights, use of market value as a compensation basis, and capacity of compensation assessors. Broadly, these factors lead to inadequate compensation and impoverishment of affected people.