<p>Mathematical creativity is important for students to reason flexibly, generate meaningful ideas, and experience mathematics as a space for exploration rather than only procedural accuracy. This multiple case study examines how three middle school students experienced and engaged with mathematical creativity during creativity-directed tasks and how they perceived opportunities for creative mathematical thinking in their regular classroom settings. Data sources included task-based interviews, observations, student reflections, group discussions, and problem-solving artifacts. Thematic analysis identified ten themes organized across three focal areas: students’ engagement with mathematical creativity, their perceived barriers to creative participation, and the influence of prior learning experiences on their creative confidence. Findings indicate that creativity-directed tasks supported students’ self-expression, deeper reasoning, collaborative idea generation, and sense of mathematical agency. In contrast, students perceived their regular classroom experiences as providing fewer opportunities for creative risk-taking and as more often validating the contributions of high-achieving or outspoken students. Implications emphasize the importance of classroom structures and pedagogical approaches that support all students as capable of engaging in creative mathematical thinking, offering guidance for designing instruction that promotes both creativity and equity in mathematics education.</p>