An episode in which students encounter difficulty while working on a challenging task can be viewed as an opportunity for them to grapple with important mathematical ideas. Teachers can use these instances to acknowledge struggle as a natural part of learning while providing appropriate guidance and support to maintain the mathematical goals and cognitive demand of the task (Smith 2000). Research suggests that a range of teacher support and responses are possible in episodes of student struggles to advance students productively toward a resolution of understanding (Warshauer 2014). This article outlines teaching strategies that remind students of the positive aspects of struggle and student actions that indicate productive engagement toward a resolution. It concludes that by incorporating instructional approaches that acknowledge student struggles and effectively support and guide the students' thinking toward a productive resolution, students are given opportunities to strengthen their disposition toward engaging in challenging tasks. Over time, they will persist through their effort to make sense of and understand important mathematics.