As the impacts of climate change intensify globally, scholars and policymakers are increasingly interested in determining the factors that lead to the success or failure of climate adaptation strategies. This paper investigates the well-being outcomes of ex-pastoralists in northern Kenya who have migrated to towns in response to severe droughts. Focusing on Marsabit Town, the study employs a comparative design with primary survey data to analyze the well-being outcomes resulting from migration as an adaptation strategy. We contrast two heterogeneous groups of former pastoralists: a “settled group” that was already residing in Marsabit Town before ending their pastoral activities and a “migrant group” that relocated to Marsabit Town at the time of abandoning pastoralism. Our analysis reveals significant differences in well-being outcomes between these groups, with the migrant group often experiencing deterioration in their well-being levels. Key predictors of poorer well-being outcomes include the loss of all livestock, informal housing, and failure to transition into agricultural work, which often results in dependence on casual labor. Additionally, many migrants continue to experience poor subjective well-being—referring to their personal satisfaction with the quality of life—years after their livelihood transition. These insights offer a nuanced understanding of the well-being outcomes of migration-as-adaptation among heterogeneous groups of ex-pastoralists and underscore the need for customized livelihood support strategies for the most at-risk populations.