This paper investigates how parents from different socioeconomic backgrounds support their teenage children in upper secondary education and how this influences their educational pathway. Based on 31 in-depth qualitative interviews with former participants of the BiKS-panel-study, this study combines qualitative insights with longitudinal data to examine mechanisms of educational inequality. While much research contrasts broader social groups, this paper also uncovers in-group-variation. The results reveal differences not only between non-academic and academic parents but also within the group of academic parents, especially between educational insiders (teachers) and outsiders (parents with university degrees in other subjects). Educational insider parents can better recognize educationally relevant opportunities, situations, and decisions and provide appropriate support because they have access to more relevant resources and field-specific knowledge. They do not intervene consistently but instead recognize when intervention is ‘necessary’ within the specific educational system, resulting in educational advantages for their children.