Poverty reduction and sustainable land management are two objectives that most African countries strive to achieve simultaneously. In designing policies to achieve these objectives concurrently a clear understanding of their linkage is crucial. Yet there is only limited empirical evidence to demonstrate the linkage between poverty and land management in Africa. Using Uganda as a case study, this analysis seeks to better understand this linkage. We used several poverty measures to demonstrate the linkage between poverty and a number of indicators of sustainable land management. In general we found a strong linkage. The results for many poverty indicators give credence to the land degradation–poverty trap, although some indicators showed negative association with land degradation. These results suggest that certain poverty reduction strategies being implemented through agricultural modernization in Africa can achieve win-win-win outcomes, simultaneously increasing productivity, reducing poverty, and reducing land degradation. Examples of such strategies include promoting investments in soil and water conservation and agroforestry. Some strategies—such as road development, encouragement of nonfarm activities, and promotion of rural finance—appear to contribute to positive outcomes without significant tradeoffs. Other strategies are likely to involve trade-offs among different objectives. The presence of such trade-offs is not an argument for avoiding these strategies; rather it suggests the need to recognize and find ways to ameliorate such negative impacts where they occur. For example, incorporating teaching of the principles of sustainable agriculture and land management into educational curricula, and into the technical assistance approach of the National Agricultural Advisory Services and other organizations, is one important way of addressing such trade-offs. Investment in poverty reduction and agricultural modernization by itself is not sufficient to address the problem of land degradation in Uganda; it must be complemented by greater efforts to promote sustainable land management practices.