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This study explores how student-generated questioning (SGQ), supported by the AI-based platform Ask.SMILE, fosters critical thinking in preservice teachers (PSTs). Implemented across three semesters in a teacher education course, students generated questions and received AI feedback aligned with Bloom’s Taxonomy. Using mixed methods, including linear mixed-effects modeling and Structural Topic Modeling (STM), the study analyzes the evolution of question complexity, inquiry themes, and correlations with assignment performance. Findings show that repeated questioning improves cognitive complexity over time, topical scaffolding shapes inquiry focus, and reflection scores better capture critical thinking than AI-level ratings. This work contributes to the scholarship on AI-enhanced inquiry-based learning and hybrid assessment in teacher education.