Tasks have been identified as playing an important role to knowledge workers as high-level units for organizing their information. TaskTracer is a task-aware desktop system that leverages the semi-automatic association between tasks and information to provide intelligent assistance to the user. TaskPredictor is a component that attempts to automatically predict the current task of the user. Our experience with TaskPredictor tells us that there still remain challenges to increasing acceptance by users. We describe our approaches to reduce the number of interruptions to the user, and to improve the accuracy of predictions.