Previous research has shown that social inequalities in the transition to higher education are a persistent phenomenon in Germany. Additionally, studies indicate that graduates from vocational schools are less likely to enter higher education, compared to their peers who graduated from general schools. However, research is scarce about how social background effects may differ for graduates from vocational schools in comparison to general schools. This paper aims to examine this twofold inequality, by introducing personality traits as resources that support graduates from disadvantaged social backgrounds to enter higher education, especially if they graduated from vocational schools. Therefore, this study distinguishes between graduates from general schools, as well as from vocational schools with a general and a specific higher education entrance qualification. Drawing on data of the two most recent cohorts of the school leaver cohort of the German Student Life Cycle Panel, logistic regression models with interaction terms are employed and average marginal effects are reported. The findings reveal that, although vocational schools are less socially selective in their student decomposition as well as in the transition into higher education, inequalities based on social background persist. Two of the five personality traits showed significant positive effects for graduates from disadvantaged social background for entering higher education: while openness appears to be beneficial for students who graduated from general schools and vocational schools, agreeableness is especially advantageous for students who graduated from vocational schools with a specific higher education entrance qualification. This paper highlights how personality traits can mitigate social inequalities in higher education transitions and underscores the importance of distinguishing social background effects across different school types. The results have broader implications for addressing educational inequalities and understanding the role of individual resources in diverse institutional contexts.