"Help! I'm stuck!" How many times have you heard a student make a similar plea? What do you consider when deciding how to respond? What reasoning is most productive? As part of a large research project, the authors explored these questions with 131 prospective and practicing teachers and found patterns in their reasoning. They began their project by sharing a video of a one-on-one conversation that took place in June between a teacher and Rex, a kindergartner. After showing the video, the authors asked the teachers in their study to provide a response. Four samples of these written responses are presented. The range of goals and teacher moves proposed in these responses highlights the inherent ambiguity in teaching--a teacher must always choose among multiple paths when supporting a child during problem solving. Children often have ways of thinking about mathematics that differ from adult ways, and research has shown that instruction that builds on children's ways of thinking can lead to rich instructional environments and gains in student achievement. (Contains 1 figure.)