Grade retention decisions are high-risk because this practice can significantly affect students' academic and professional path and their socioaffective development. This study aimed to contribute to a better understanding of second-grade retention decision-making by exploring the factors the professionals consider during the retention decision-making, their beliefs about the effectiveness of grade retention, and their cognitive decision-making style. The study sets in Portugal, where second-grade retention is a common practice. One hundred ninety-four teachers answered an online questionnaire developed for this purpose. Path analysis results suggested that teachers' beliefs and decision-making styles served as a filter, defining what factors they consider relevant or not to make grade retention decisions. Intuitive experiences seem to inform teachers' grade-retention decisions, especially when they believe retention is essential for students' success.