Women in academia are typically outnumbered by men, a phenomenon metaphorically known as “the leaky pipeline.” This study contributes by showing a motherhood penalty in the career pipeline at the postdoctoral stage in Germany—that is, during habilitation. Based on CV information and an email survey, the paper examines which factors are associated with being awarded a habilitation and whether these factors differ between women and men as well as mothers and fathers. Using Cox regressions of retrospective career trajectories of almost all psychologists at German universities in 2019 (2,527 scientists with 37,423 publications), the study shows that SSCI/SCIE articles and having a PhD from abroad increase the habilitation risk more strongly for women and mothers than for men and fathers. Net of career factors observed by CVs, however, mothers have a 42% significantly lower habilitation risk.