This chapter examines encroachment in an African and South Asian context by comparative case studies of land grabs in the United Republic of Tanzania and squatting in the Federal Republic of Nepal. The chapter demonstrates that today’s sites of encroachment are related to past national development efforts. Of specific interest is the manner in which land reform contributes to the conditions of encroachment through the creation of varied and competing categories of land and claimants. Multiple claims to land, in turn, create sites of ambivalence, contestation, and opportunities for land grabbing and occupation. Special attention is paid to the inadvertent effects that land reform had in each country through displacement, impoverishment, and the creation of ambiguity and the subsequent contestability of tenure. The chapter concludes by underscoring the deleterious effect that land reform had on the most vulnerable sectors of society through economic hardship, lack of political and economic recourse, and dispossession.