Teachers can influence the learning of students to a greater extent if encounter manageable challenges whereas they are often trapped with situations that reduce their teaching efficacy to a bare minimum. They fail to address their students' academic and non-academic needs because they fail to notice the expressed needs. This situation stimulates the researcher to explore the challenges encountered by the teachers to support the learning of students. The study employed a qualitative research design and case study method was used to explore the perspectives of the participants. The research population consisted of school administrators, school teachers, and students at secondary schools. Purposive sampling technique was used to choose the sample against the predefined criteria. The data was collected through semi-structured interviews, field notes, and notes from document analysis. Triangulation of the collected data resulted in the development of three themes namely extensive subject outline, managing exceptional and behavioural responses. The findings showed that the teachers are experiencing many challenges such as lengthy syllabi, overcrowded classrooms, demanding assessment structures, additional academic responsibilities, and students’ behavioural issues and this is affecting their ability to positively influence the learning of their students. The study suggests that teachers should use their critical thinking skills to analyze their personal and professional challenges and find ways to resolve these issues resulting in creating supportive learning structures in schools for students, and teaching culture for teachers. This study will help school administration understand the barriers faced by teachers in schools and help them find suitable solutions to provide a supportive teaching and learning environment for teachers and students.