This paper describes a self-study research project that focused on our experiences when planning, teaching, and evaluating a course in initial teacher education. The theoretical framework of technological pedagogical content knowledge (TPACK) was used as a conceptual structure for the self-study. Our understanding of the framework in relation to our teaching practice was in focus. The principal educational goal of the course was to develop the pedagogical use of web 2.0 resources to support learning in the preschool/school context. As a result, the focus, content, form of distribution, teaching, and assessment of the course went beyond what is common in initial teacher training in Sweden. The potential of the different digital tools was explored by situated use in the design and teaching of the course. Analysis highlights the challenges and opportunities that teacher educators and student teachers may encounter while working with, and learning about, information and communication technologies to support learning. Some of the findings discussed are related to the identified challenges and opportunities for both teachers and students to integrate content knowledge, pedagogical knowledge, and technological knowledge into a TPACK. Taken-for-granted organizational and institutional assumptions about teaching, learning, and assessment in teacher education were identified in the study. (Contains 1 figure.)