This study aims to determine students learning obstacles in probability material based on their probabilistic thinking (PT) level using the theory of didactical situation (TDS) perspective. This is qualitative research with the case study method. The subject consisted of 23 grade 9 students in junior high school who had studied the material and had taken the test. The test results were used to classify students depending on their PT level using the framework developed by Graha A. Jones. Furthermore, interviews were performed with three representative students from each PT level. The interviews indicated that students in each PT level continue to face learning obstacles, which include instrumental ontogenic and epistemological obstacles. The lowest PT level demonstrated a more complex and comprehensive learning obstacle in all constructs of PT. From the TDS perspective, all students who are at various levels of PT have reached an action situation. Only 33% of the students at the subjective level and 83% of the students at the transition level reached the formulation situation. Still, students at that level needed help to reach the other two situations. Unlike the two previous levels, students at the level of quantitative informal thinking can achieve situations of validation and institutionalization.