This article sets out to describe and explain how four high school teachers, identified as improvement-oriented teachers (IOTs), in their day-to-day teaching, try to use pedagogical remedies to help their students overcome the difficulties that hinder in-depth learning in secondary mathematics classrooms. Providing reflective accounts from the IOTs’ experiences and presenting illustrative examples from their classrooms, the study provides a broad picture of the context in which students learn mathematics. The study recognizes the factors that constrain students from gaining in-depth understanding into subject matter knowledge; it highlights the possibilities of fostering in-depth learning by establishing the primacy of the teacher in bridging the gap between students’ perceptive faculty of mind and subject matter knowledge. It recognizes the influences the teacher’s actions, pedagogical moves and decisions exert on students’ in-depth learning of concepts. The study also underscores the vital importance of students’ prior knowledge of basic mathematical concepts in in-depth learning of new concepts. Implication of the results of the study underscores the need for synergy of efforts on the part of teacher, school, and other key stakeholders, and curriculum in creating and promoting an environment conducive to students’ in-depth learning in mathematics.