This paper studies how relationship-specific learning affects the joint dynamics of exports and trade finance. Using micro-level Chilean data, it documents that new exporters initially rely on cash-in-advance payments and gradually transition to providing trade credit as relationships mature, with faster transitions in riskier destinations and for less experienced firms. Motivated by this, the paper develops a general equilibrium trade model that integrates learning about foreign demand and counterparty risk together with firms’ endogenous export and trade finance choices. The model is used to investigate the role of learning and risks in shaping export adjustments and quantify the impact of shocks to the cost of trade finance on aggregate exports. The analysis finds that the response to these shocks depends on the riskiness of the destination and is amplified by the disruption of long-term trading relationships.