Cases are used to support situated learning in professional education because they contextualize learning and promote apprenticeship-like discussions between instructors and students. Recent work in case-based reasoning (CBR) reinforces important implications of situated learning, authentic activity as simulated experience by providing expert exemplary cases, and authentic tasks and activities. As novices engage CBR learning environments, they participate in social practices and develop context-based case knowledge, design strategies, and socially shared identities and beliefs. This study examined how preservice teachers gain situated knowledge about teaching with technology by engaging the experiences of practicing teachers through Web-enhanced CBR. All students in the class were involved in Web-enhanced CBR projects and were provided expert teachers exemplar case libraries and scaffolds via a Web-based, case-based doing tool (CBDT). Five preservice teachers, purposefully selected as participants, were interviewed throughout the semester, and artifacts of their reasoning were collected. Constant comparison techniques were used for data analysis. Major findings indicated that participants perceptions and understanding of computers educational roles evolved from simple tools for productivity and motivation to diverse and advanced roles for learning concepts and developing thinking skills. They also developed critical concepts related to teaching with technology, including teachers roles, students characteristics, and pedagogy. This study also examined how preservice teachers, as novices, in a semester-long Web-enhanced CBR learning environment, began to develop expert-like strategies, using CBR activities to understand both the culture and practices of seasoned teachers. Preservice teachers used automatizing, analyzing, articulating, and interweaving strategies during Web-enhanced CBR activities and considered Web-enhanced CBR as a catalyst and a framework to better understand the practicing teaching community. Web-enhanced CBR activities helped preservice teachers to learn the processes of, and develop the perspectives and knowledge situated in, the teaching with technology culture.