More than 20% of all school-aged children in Germany experience a grade retention and repetition during the educational career which is likely to affect their well-being as a central element of school success. This study aims at revealing the temporal dynamics of general and school well-being around the event of grade retention (i.e., the year when the decision to repeat a grade is taken) and the subsequent grade repetition (i.e., the repeated school year) during secondary school in Germany. Longitudinal data from the National Educational Panel Study (NEPS) is used on native students attending grades 5 through to 12 (N = 4581 from originally 273 schools). Distributed fixed-effects regressions by gender and school type have been conducted, using satisfaction with school and life as outcomes. Although retention decisions often trigger an immediate decrease in students’ well-being, there arise still benefits from this event in the short-term, middle-term and long-term, though trajectories differ by gender and school type. Overall, it is necessary to promote students´ well-being throughout their educational career, particularly in those critical periods when they face grade retention. Results highlight that tailored programs for both genders and students in different school types should be provided to foster well-being during this phase.