Programs that process secret data may inadvertently reveal information about those secrets in their publicly-observable output. This paper presents LeakWatch, a quantitative information leakage analysis tool for the Java programming language; it is based on a flexible "point-to-point" information leakage model, where secret and publicly-observable data may occur at any time during a program's execution. LeakWatch repeatedly executes a Java program containing both secret and publicly-observable data and uses robust statistical techniques to provide estimates, with confidence intervals, for min-entropy leakage (using a new theoretical result presented in this paper) and mutual information. We demonstrate how LeakWatch can be used to estimate the size of information leaks in a range of real-world Java programs.