In recent years, many countries within the Organisation for Economic Co-operation and Development have formulated educational policies aimed at providing better education to more students. However, this may be perceived as constituting dilemmatic spaces, where teachers must make efforts to reconcile coexisting political demands in their everyday work. The purpose of this article is to provide insight into how teachers handle coexisting educational policies of increased student retention and performance. Empirical findings from a one-year field study at a Danish vocational school explore how teachers' decision-making as response to coexisting demands of increased student retention and performance involves the development of various pedagogical approaches to the students: an active "caring" approach, a passive "wait until this class is over" approach, an active "vocational gate-keeping" approach, and a passive "wait and see whether they drop out" approach. Based on the findings, it is argued that the various pedagogical approaches are developed through social negotiations with leaders, students, and other teachers. Moreover, these pedagogical approaches lead to the development of further negotiated, dilemmatic decisions to be made. Thus, a dynamic approach to teachers' dilemmatic decision-making is proposed.