This study focused on the teaching challenges and predicaments for a novice assistant professor of an elementary educational practicum course in an university of education. The new assistant professor, who had neither training background in elementary education nor teaching experience in elementary schools, has been assigned to teach elementary educational practicum courses advising student teachers since the fall semester of 2005. Our research has begun since then. Data collection included interviews with the assistant professor, inquiring his experiences and goals of teaching. We also interviewed students, his teaching peers and colleagues to better understand the context in which the novice assistant professor teaches. Additionally, we collected course documents, such as the course syllabi, assignments, and his teaching profiles. In addition, we observed some of the classroom sessions, and a mid-semester observation and stimulated recall interview were conducted. Results show the novice professor had two major predicaments: internal predicament and external predicament. The internal predicaments involve queries from students about his professionalism, increasing difficulties in motivating students to learn, and how to deal with students dissatisfaction. The external includes difficulties in cooperating with his teaching peers, as well as lack of supports from senior faculty members. This study addresses the importance of constructing an institutional support mechanism for novice professors to overcome the challenges and predicaments involved in teaching. In doing so, they will be in a better position to interact with students and enhance the quality of teaching.