The objective of the present study was to gain a deeper understanding of how middle-grade mathematics teachers implement questions in both technology-supported and non-technology-supported classrooms. The investigation demonstrated that in-service mathematics teachers teaching in a technology-supported classroom and in a non-technology-supported classroom employed seven questioning channels: teacher-created static nature of drawings, teacher-created dynamic nature of drawings, student-created nature of drawings, student verbal discourse, a ready-to-use educational animation and textbook definition, analogies, and real-life examples. Commonly, both teachers used student-created static nature of drawings on worked examples, teacher-created static nature of drawings on worked examples, and mathematical procedures or concepts in their questioning, as well as students' verbal discourse. The integration of technology introduced three additional questioning channels in technology-supported classrooms: the teacher-created dynamic nature of drawings, a ready-to-use educational animation and textbook definition, and a real-life example. In conclusion, this study indicates that teacher questions can be influenced by the questioning channels employed, and technology might, to some extent, affect teachers' variety of questioning channels. The results are discussed in the light of related literature.