Teacher-educators' conceptions of teaching may influence their teaching practice in a variety of ways. The concept of dilemma may provide an adequate framework to disclose how teacher-educators realise their conceptions of teaching in actual teaching practice. In our view, dilemmas constitute a powerful conceptualisation to find out about the professional's beliefs concerning teaching student teachers learning to teach and the choices the teacher-educator makes with regard to teaching strategies in actual practice. Twenty-three Dutch and twelve Israeli teacher-educators were interviewed in-depth on this topic. The results were interpreted around two axes: internally or externally attributed dilemmas and student-or professionally-(i.e., self-related) attributed dilemmas. The teacher-educators identified several dilemmas about their teaching, as well as strategies to cope with them. The study showed teacher-educators were cognisant of dealing with the tensions in realising their goals, attributing them to external (i.e., conditions, students) as well as internal sources (approaches, self). Strategies to deal with them involved ways of motivating students and creating learning environments that stimulate inquiry and study, taking into account differences among students.