This study develops and tests theory about the context-specificity and outcome-dependence of experiential learning in acquisition processes. First, we investigate whether learning from experience gained in different acquisition contexts is limited to influencing subsequent outcomes of same-context transactions. Second, we analyze whether learning patterns in response to prior successes and failures differ across acquisition contexts, depending on two properties of these contexts—the degree of structural variance and the level of stimulation of deliberate learning. Learning is assessed with respect to an underexplored organizational goal variable in acquisitions: completion of a publicly announced transaction. An analysis of 4,973 acquisition attempts in the newspaper industry in 1981–2008 largely supports our theory. Copyright © 2012 John Wiley & Sons, Ltd.