Recent work in case-based reasoning (CBR) reinforces the importance of situated learning, expert cases, and authentic tasks and activities for novice learners. As novices engage CBR environments, they apprentice in the experts' practices while developing the understanding, knowledge and skill of a given community. This study examined how prospective teachers, as novices in a semester-long course, engaged and developed expert-like practices using the case knowledge of experienced teachers who teach with technology. By engaging experienced teachers' knowledge and skill via Web-enhanced cases, prospective teachers refined their understanding of teaching culture and teaching with technology as they transitioned to the teaching community.