Mathematics word problems provide students with an opportunity to apply what they are learning in their mathematics classes to the world around them. However, students often neglect their knowledge of the world and provide nonsensical responses (e.g., they may answer that a school needs 12.5 buses for a field trip). This study examined if the question design of word problems affects students' mindset in ways that affect subsequent sense‐making. The hypothesis was that rewriting standard word problems to introduce inherent uncertainty about the result would be beneficial to student performance and sense‐making because it requires students to reason explicitly about the context described in the problem. Middle school students (N = 229) were randomly assigned to one of three conditions. In the standard textbook condition, students solved a set of six word problems taken from current textbooks. In the modified yes/no condition, students solved the same six problems rewritten so the solution helped answer a “yes” or “no” question. In the disfluency control condition, students solved the standard problems each rewritten in a variety of fonts to make them look unusual. After solving the six problems in their assigned condition, all students solved the same three “problematic” problems designed to assess sense‐making. Contrary to predictions, results showed that students in the modified yes/no condition solved the fewest problems correctly in their assigned condition problem set. However, consistent with predictions, they subsequently demonstrated more sense‐making on the three problematic problems. Results suggest that standard textbook word problems may be able to be rewritten in ways that mitigate a “senseless” mindset.