The world of mathematics education is progressing rapidly with new knowledge being generated through advanced research. In order to make sense of the new mathematical discoveries and information in the field of mathematics education, conceptual understanding of mathematical concepts is very essential. Moreover, mathematics teaching and learning to promote students’ conceptual understanding in the context of Pakistan is considered challenging. Nevertheless teachers try to handle the emerging challenges while teaching for conceptual understanding. This study aimed to explore the challenges of mathematics classrooms and the strategies that mathematics teachers use to promote mathematical understanding in the middle school of a private Learning Resource High School in the context of Gilgit-Baltistan. In order to achieve the research purpose, a qualitative case study approach was used to carry out this study. The participants of this study were two mathematics teachers. The tools used for the purpose of data collection were: semi-structured interviews, classroom observations, post lesson discussions, document analysis and reflective journal maintained by the researcher. The interview data was audio-taped and transcribed. Further, the data was analyzed by coding and categorizing under various themes. The study revealed that during the teaching and learning of mathematics, teachers face certain types of challenges such as English language barrier, non-availability of teaching resources and their utilization, lack of classroom culture of exploration and issues in teaching of algebraic concepts. Similarly, the study also revealed that to overcome the emerging challenges, the teachers facilitate students with the help of contextual low-cost no-cost materials, contextualizing the mathematical concepts and through the involvement of the students. This study can help mathematics teachers and educators to design various types of activities to overcome the challenges.