This multi-case study investigated self-regulation of preservice science teachers' (PSTs), focusing on their ability to learn from their own teaching experiences and to regulate teaching practices to pose higher-level cognitive questions. The participants were three PSTs enrolled in a certification program for teaching secondary science, representing low, intermediate, and high self-regulated learning (SRL). Data were collected from classroom materials, semi-structured interviews on planning classroom questions, classroom observations, classroom audio recordings, and semi-structured interviews on enacting questions. The findings revealed that while each case exhibited unique characteristics, all PSTs demonstrated improvements in their SRL practices and questioning. The analysis highlighted PSTs' SRL practices in planning and enacting classroom questions, suggesting ways to enhance PSTs' questioning skills through the integration of SRL into teacher preparation. Furthermore, the findings underscored the importance of university supervisors and cooperating teachers tailoring their coaching to PSTs based on their initial SRL skills and utilizing well-defined models of SRL development for guidance.