Land dispossession and conflicts over land compound resettlement efforts in post-conflict contexts. This is particularly true in rural sub-Saharan African countries, where the vast majority of livelihoods depend on maintaining access and rights to cultivable land. This article engages in the active debate on this topic using ethnographic research conducted in the Teso region in eastern Uganda during 2012 and 2013. The Teso region experienced three violent conflicts from the late 1960s to the mid-2000s, which at times were overlapping: large-scale cattle rustling, a civil war, and an insurgency. The research focuses on Amuria District, Katakwi District, and Tisai Island in Kumi District in order to consider three interrelated phenomena: the cyclical nature of the displacement-resettlement process, the intra-regional differences in how this process has unfolded, and the particular ways in which struggles over land are deeply embedded within the post-conflict context. The article argues that post-conflict rearrangements in property relations create complex challenges for resettling populations, and if left unaddressed will merely result in increasingly unstable land tenure regimes. It also argues that struggles over land in Teso should not be understood solely through a post-conflict lens, as there are a variety of drivers – some not tied directly to the violent conflicts – that interact with post-conflict dynamics to create a perfect storm for land tenure instability.