Abstract: SMILE (Stanford Mobile Inquiry-Based Learning Environment) is a technology developed to support student learning through student-generated questioning. Literature has shown that student-generated questions can positively affect students’ learning motivation and reading comprehension, depending on teachers’ design of learning activities. To explore ways that teachers may use SMILE to support student-generated questioning practices, we piloted it with 26 preservice teachers. They used SMILE to enact student-generated questioning practices that elicit and use higher-order thinking in the learning process. We evaluated questions generated by teachers and reported their implementation experience with K-12 students. Our paper discusses teachers and students’ sense of achievement with student-generated questioning practices, perceived satisfaction, and challenges of using SMILE to enhance student-generated questioning practices in the classroom.