Drought is a recurring challenge to the livelihoods of those living in Tharaka District, Kenya, situated in the semi-arid zone to the east of Mount Kenya, from the lowest slopes of the mountain to the banks of the Tana River. This part of Kenya has been marginal to the economic and political life of Kenya from the colonial period until the present day. A study of more than 30 years of change in how people in Tharaka cope with drought reveals resilience in the face of major macro-level transformations, which include privatisation of landownership, population growth, political decentralisation, increased conflict over natural resources, different market conditions, and environmental shifts. However, the study also shows troubling signs of increased use of drought responses that are incompatible with long-term agrarian livelihoods. Government policy needs to address the challenge of drought under these new macro conditions if sustainable human development is to be achieved.