Problem solving is an essential aspect of students' mathematical activities. This ability could practice by using heuristic strategies in learning. Besides, these are assured to be able to promote metacognitive skills. In the implementation, teachers faced several challenges. This research aims to describe the challenges of teachers in implementing learning with heuristic strategies. This research is a descriptive qualitative. Participants of this research were 12 junior high school mathematics teachers from 12 high schools in the Special Region of Yogyakarta and Central Java. Data collection was taken by questionnaire and added with documentation. Data were analyzed using the Miles and Huberman stage-data reduction, data display, and drawing conclusion/verification. The data then validated using triangulation technique. The results revealed that some of teacher has already implement heuristic strategy in the learning process, but unable to define the heuristic strategy correctly. In its implementation, teachers experience several obstacles. These obstacles were found in providing non-routine problems to students, solving problems by students, and in discussions conducted to solve problems.