Guided listening is vital in music education, fostering self-expression, skill development, and academic achievement. Yet, its limited use in Israeli high schools creates a gap between its recognized value and practice. This mixed-method study examines guided listening integration in secular Jewish-Israeli high school music programs based on four philosophical and pedagogical approaches—esthetic, Praxial, active, and peer instruction—to understand teachers’ objectives, methodologies, implementation, and optimal learning environments. Data was collected from an online questionnaire, structured interviews, direct observations of Western Art Music History lessons, and the researcher’s reflective journal. Key findings: (1) teachers tend to use a repeated five-step teaching pattern (reviewing, lecturing, analyzing, listening while following a score, summarizing); (2) teachers usually do not write lesson plans with detailed, step-by-step guidelines; and (3) teachers use recommended guided listening approaches in a limited capacity, likely due to pressure from preparing students for exams, and the perception that such methods are not fully suitable for Israeli high school music students. The paper explores teachers’ challenges in adopting guided listening pedagogical methods while balancing curriculum demands and promoting inclusivity. It offers recommendations for policymakers and educators on professional development and curriculum revisions, emphasizing detailed lesson planning for effective learning outcomes.