The policy learning literature indicates that governments can and do learn after a policy failure but not always. The purpose of this study is to examine the conditions under which policy failure leads to policy learning. It asks two questions. First, is policy failure associated with policy learning? Second, if policy is associated with policy learning, does the failure initiate different types of learning? Using the policy failure and learning literatures as an organizing framework, this paper analyzes three comparative cases of policy failure revealed by tornados in Greensburg, Kansas (2007); Joplin, Missouri (2011); and Moore, Oklahoma (2013). It finds that failure of the policy process in agenda setting is associated with instrumental policy learning. It also finds that there are two types of failure of decision making: failure to make a timely decision and failure to make any decision. The two types of decision-making failure are associated with different types of policy learning. In addition, the contextual factors underpinning the link between policy failure and learning are prior experience with the policy problem and capacity to learn.