This research (the second part of a 2-part study) sought to investigate selected high school teachers’ knowledge and use of a problem solving approach to mathematics teaching and learning. It also examined the challenges that they experienced in implementing this pedagogical approach. A survey research design was used for this research whereby data were collected using a questionnaire with closed- and open-ended items. Thirty-one high school teachers from Jamaica participated in the study. The findings indicated that the teachers generally used a problem solving approach during instruction very regularly and felt extremely competent when using the approach. Some of the most frequently reported challenges included students’ lack of interest and tenacity in solving problems; teachers’ heavy workload; and the time consuming nature of the approach. One key recommendation to address the challenges raised is implementation of professional development for teachers to guide them in effectively incorporating problem solving as a teaching/learning approach in the mathematics classroom.