The relationships between mentors' (n = 168) attachment dimensions, the quality of mentoring relationship and protégés' (n = 187) level of adjustment after 8 months of mentoring intervention were explored. Unexpectedly, protégés of mentors with moderately negative childhood experiences and an insecure state of mind had higher levels of adjustment at the end of mentoring, whereas mentors' positive emotional childhood experiences contributed negatively to levels of adjustment. Furthermore, a dependent mother–protégé relationship moderated the relationship between mentors' attachment anxiety or avoidance and the quality of the relationship, such that it mediated the relationship between mentors' attachment anxiety and avoidance and led to a decrease in protégés' level of adjustment at the end of the intervention. The findings suggest that the disadvantages of a dependent mother–protégé relationship as regard protégés' level of adjustment interact with mentors' avoidance or anxiety, and that there may be an advantage in a mentor–protégé mismatch in terms of an anxious/dependent relational history.