Research shows that the greatest gains in student learning in mathematics classrooms occur in classrooms in which there is sustained use of high cognitive demanding tasks throughout instruction (Boston and Smith 2009). High cognitive demanding tasks, which this article will refer to as rich tasks, are mathematics problems that are complex, less structured, and can take longer than other typical problems to solve because they require students to "think about, develop, use and make sense of mathematics" (Stein, Grover, and Henningsen 1996, p. 459). Such tasks also afford students and teachers the opportunity to "make sense of problems and persevere in solving them," one of the Common Core mathematics standards (CCSSI 2010). This article builds on Smith and Stein's idea of anticipating student solutions for a cognitively demanding algebra task by providing several possible student pathways and teacher responses that allow teachers and students to engage with the Common Core mathematics practice of making sense of problems and persevering in solving them. A cognitively demanding algebra task, Skyscraper Windows, is presented that allows students to consider multiple algebraic representations when solving problems.