Empirical evaluation of software systems in actual use is critical in software engineering. Prototyping, beta testing, and usability testing are widely employed to refine system requirements, to detect anomalous or unexpected system and user behavior, and to evaluate software usefulness and usability. The World Wide Web enables cheap, rapid, and large-scale distribution of software for evaluation purposes. However, current techniques for collecting usage data have not kept pace with the opportunities presented by Web-based deployment. This paper presents an agent-based approach and prototype system that makes large-scale collection of usage data over the Internet a practical possibility.