Students need to be challenged to stimulate their learning. Applying challenge in practice however is not straightforward. Challenging students may conflict with other teacher responsibilities, creating potential dilemmas for teachers. This study discloses dilemmas teachers encounter when challenging students as well as the considerations accompanying their actual choices for action when coping with these dilemmas. Based on interviews with teachers, first, a dilemma analysis instrument was developed. Seven main categories of dilemmas were found. One of the main dilemmas encompassed maximizing challenge versus keeping all students on board. University students differ in their ability, confronting teachers with the feeling that choosing to serve one group could be detrimental to the learning of others. The diversity of choices and considerations brought forward by the teachers indicates that it matters who the teacher is, and what he or she stands for and is able to do.