It is important for students to be successful in their academic lives, both for themselves and their families. Some certain individual obstacles on the path to success can diminish students' achievement as well as their motivation, which is a crucial factor for success. Sometimes parents can be involved in these processes. In this context, the current study aims to examine the mediating role of academic motivation in the relationship between high school students' academic self-handicapping behaviours and their subjective academic well-being, as well as the moderating role of perceived parental pressure for academic achievement in this relationship within the framework of the self-determination theory. The study group consists of 721 students (419 girls and 302 boys) attending high schools in Türkiye. Subjective Academic Well-Being Scale, Academic Self-Handicapping Scale, Academic Motivation Scale and Parental Academic Achievement Pressure and Support Scale were used to collect data in the study. The results revealed that academic self-handicapping behaviours significantly and negatively predicted students' subjective academic well-being. Moreover, it was found that academic motivation had a mediator role in the relationship between academic self-handicapping behaviour and subjective academic well-being. In addition, it was found that parental academic pressure had a moderator role in the relationship between academic self-handicapping behaviour and academic motivation and in the indirect effect. According to the results, students' academic self-handicapping behaviours have a direct effect on their subjective academic well-being as well as an indirect effect through academic motivation. Furthermore, it was found that the indirect effect of students' academic self-handicapping behaviours on their subjective academic well-being varies depending on the level of perceived parental pressure for academic achievement. In light of the findings obtained, theoretical and practical suggestions are made.