<p>Incorporating student-generated questions (SGQ) into teacher education powerfully promotes preservice teachers’ (PSTs) critical thinking, agency, and instructional design skills. Despite these benefits, SGQ remains underutilized in many educational contexts. Fortunately, structured interventions for SGQ that integrate scaffolding frameworks such as Bloom’s Taxonomy can significantly enhance students’ ability to think reflectively and critically. This study investigates how PSTs develop critical thinking through SGQ using Ask.Smile across three semesters (<i>n</i> ≈ 90; 8,576 questions). Data analyses included descriptive statistics, linear mixed-effects modeling, correlation analyses, and structural topic modeling. Results show that PSTs’ question levels improved with repeated attempts, supporting the iterative nature of critical thinking and the value of AI feedback. Topic modeling revealed that when topical constraints were absent, students often posed personally oriented or real-world questions, while later semesters showed more academic focus under more instructional guidance. Findings highlight how instructional design shapes both the quality and nature of inquiry, suggesting that balancing autonomy with scaffolding can foster creativity. Moreover, weak correlations between question levels and assignment grades highlight the complementary role of reflective writing in capturing critical thinking. Overall, this study demonstrates SGQ’s potential, particularly when paired with AI tools, to enhance PSTs’ inquiry and critical thinking.</p>