In 2002, IPFW adopted a web application to enhance the recording and reporting of clinical education experiences of nursing students. This web application, known as the Essential Clinical Behaviors (ECB) system, is an on-going, joint effort between the Computer Science and Nursing Departments. It replaced a tedious and error-prone method, based on printed forms and informal reports, for tracking the practice of nursing skills. Since Fall 2005, the ECB has been a mandated part of every clinical nursing course. The goals of the ECB were three-fold: (1) to foster more self-directed learning; (2) to enable clinical instructors to increase the diversity of clinical experiences for their students; and (3) to facilitate the collection and analysis of data for accreditation reviews. In this paper we discuss the progress made in—and some surprising obstacles to--achieving these goals. We also discuss the evolution of the ECB in the last four years to increase its usability, and the impact it has made on the nurse education process itself.