Today teacher educators emphasize the need for preservice teachers to develop certain habits of mind (like reflection) in order to be effective teachers. These educators are constantly searching for pedagogical strategies that can help teachers quickly learn, understand, and take to heart important dispositions. This article describes a three-year research project that explored the computer conferencing experiences of practicing teachers who were involved in a two year, nontraditional master's program. In this study it was found that web-based conferencing can provide a valuable pedagogical tool that reinforces content and encourages the development of important dispositions, but it can also perpetuate the very habits of mind that teacher educators want to change. This article illuminates the difficulties of implementing progressive strategies as researchers seek to understand how conferencing can provide added instructional benefit to programs that promote transformative teacher education