Modeling caring behavior, role playing, and creating and enforcing classroom and school rules are all time-honored strategies used by teachers to create classroom environments that foster safety, empathy, a sense of belonging, and respect for self, others, and property. During times of crises in children's lives, these strategies are heightened in importance. Administrators, classroom teachers, school counselors, psychologists, and other school staff members are expected--often without warning--to lead students through times of fear, anger, mistrust, and grief. Many education professionals experience feelings of inadequacy about how to handle difficult situations that arise in the lives of their students, and yet caring educators have responsibilities to students and to themselves during times of crisis. This article provides helpful guidelines for classroom teachers when confronted with two potential crises that affect students: death and divorce. Teachers who become more knowledgeable about how students may behave during these times and who equip themselves with strategies are empowered with the ability to transform these teaching dilemmas into teachable moments. During these moments, students gain insight and learn valuable life lessons from the teacher and from one another.