Formal education is one of the most influential predictors of professional success. As parents in Germany are aware of the importance of education, they often try to enable their children to enrol in the prestigious academic schooling track (Gymnasium). This explains why the transition recommendation made by the teacher after the fourth grade is sometimes ignored if the desired track was not recommended for a particular student. How the mismatch between the teacher’s recommendation and the parents’ choice of schooling for their child affects the child’s development is not sufficiently known. It is very likely that such a mismatch can have consequences for the child’s well-being, competences and overall academic success. Based on five consecutive panel waves of German National Educational Panel Study (NEPS) data (waves 1 to 5, collected between 2010 and 2016) (n = 2;790 in wave 1), our analyses demonstrate that social background and the probability of ignoring a teacher’s recommendation are associated, and that highly educated parents are more likely to overrule the teacher’s recommendation. Panel regression models show that pupils who pursued the academic track (Gymnasium) despite the absence of a teacher’s recommendation were more likely to drop out of the academic schooling track, and were not able to catch up with their peers with respect to both objective and subjective academic competences over the entire observation window. However, the models also show that academic track mismatch did not seem to negatively influence the health and well-being of these pupils.