Rangeland degradation, with the loss of perennial grasses and shrub encroachment, negatively affects livestock production and reduces the drought resilience of commercial ranchers and pastoralists in drylands. This situation applies in Namibia, where few attempts have been made to investigate rangeland changes and shrub encroachment across the two major land-tenure systems in the country, namely, freehold and communal land. This study aimed to investigate the inter-relationships among rangeland changes, land tenure and management in Namibia within the past 55 years, by combining remote-sensing analysis, literature review, and interviews. Land-cover classification results revealed different trends in the two tenure systems between 1965 and 2020. Both were affected by shrub invasion. At the onset of the observation period, the percentage of grass-dominated savanna was higher on communal land. Whereas a linear increase in shrubland was observed after 1965 on communal land and on freehold land up to 2001, the shrub encroachment trend on freehold land reversed from 2011, mainly because of de-bushing measures. The most important drivers for rangeland changes and shrub encroachment were related to specific land-management practices and the historical and socio-economic contexts in which they occurred, including various policies associated with colonialism, fire suppression and overgrazing, combined with recurrent droughts. Although farmers on freehold land apply various strategies to combat shrub encroachment, the aftermaths of colonial policies and the issues of common-pool resource management have limited the options of those on communal land to implement such measures. The search for sustainable management options, thus, requires a deeper understanding of their potentials and shortcomings in both land-tenure types; such understanding could be acquired by considering local knowledge and past and current land-use practices. Management options that incorporate the numerous benefits of woody plants and the uses of shrubs hold promise for sustaining livelihoods in both land-tenure systems.