The historical record has much to teach when it comes to the nature of confidence building techniques, the circumstances of CBM use, and the probability that a given CBM will produce some result. For one thing, it is clear that what have in the past been used to build confidence in fact represent a very broad range of options compared to the usual list of measures one frequently hears discussed today. Second, it is apparent that detailed operational preplanning in anticipation of certain types of crisis situations is, by and large, a fruitless task: in particular, the most promising options tend to emerge only as the specific features of a scenario come into sharp focus. Third, in the gravest crises, CBM have tended to accomplish little or nothing. To illuminate these lessons, this paper dissects historical cases using an historical framework for the evaluation of CBM. The cases used include the Anglo-French Rivalry of the nineteenth century; the Don Pacifico Affair, 1850; the Fashoda Crisis, 1898; the Balkan Crises, 1912-1914; and Munich and Danzig, 1938-1939.