Amid the proliferating uncertainties of globalised modernity, development institutions have deployed insurance to transfer risk across more geographic and hazard domains. This chapter first explores why insurance and other risk transfer tools are increasingly popular responses in development practice. It then argues that this embrace can paradoxically proliferate uncertainties when insurance contracts fail to pay out, illustrated with reference to drought insurance in Malawi and pandemic insurance in the Democratic Republic of Congo. The chapter closes by envisioning how insurance might be refashioned from a ‘technology of hubris’ to a ‘technology of humility’, suggesting some principles for more relational deployments of insurance that could begin to recuperate its promise as a technique of mutual solidarity and sustainable risk-sharing.