This chapter analyses principals’ encounters with the unforeseen, based on qualitative in-depth interviews with eight principals who have experienced unforeseen events. The purpose of this study is to gain deeper insight into what seems to be important when facing and enduring the unexpected. The aim is to provide language and concepts to assist school leaders to be mentally prepared to face and exercise practical wisdom when faced with the unforeseen. The theoretical perspectives this chapter builds upon are professional judgment and practical prudence. This study has been centred around the international research tradition associated with practical prudence towards a leadership perspective. An analysis of the findings shows that dealing with one’s own and others’ emotions, the need for collaborative support, the duty to act and endure, as well as processing the event afterwards, are central. These events may lead to a lengthy process, and the people involved will have to continue to collaborate both during and after the situation. Although the intensity of the school cases is not as dramatic as for other professionals who must face demanding, unforeseen situations daily, it is still highly challenging for principals. In school, serious unforeseen events are rare. Still, this chapter argues the importance of including this topic in both the teacher and principal education programs in a time where faith in evidence-based knowledge, rules, routines, and procedures is great, whereas the room for discretion adapted to the context-specific situation seems to be diminishing.