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. Practitioner Points Teachers considered up to 12 factors when deciding whether to retain or promote a second‐grade student. Teachers' decisions are shaped by their beliefs and intuitive experiences, influencing the factors they consider relevant during the decision process and, ultimately, the decision to retain or not a student. Intuitive experience informs teachers' retention decisions by maintaining their beliefs in the effectiveness of grade retention and guiding the factors considered during the decision‐making.