In this paper, we use a discrete choice experiment conducted among pastoralists in four different semi-arid counties in Kenya characterized by different land tenure regimes to analyze how pastoralists make tradeoffs between tenure security and grazing flexibility - the so-called pastoralist paradox. Results show that there is one group of respondents who are desperate for change and seem to prefer either group or private title deeds to their current situation. A second, smaller group has strong preferences for the status quo, which could be driven by their relatively short migration distances. Concerning index-based livestock insurance, the basis risk suffered by insured pastoralists due to underprediction is high, but willingness to pay (WTP) for livestock insurance should still be high enough to ensure maximum uptake, leaving current low uptakes hard to explain. The worry about climate change is high but does not translate into increased WTP for more secure tenure or formal livestock insurance.