In the Netherlands, as in many countries, there is a growing use of shadow education: fee-based, organized, out-of-school learning activities that provide students with instruction or guidance in school subjects. Its increasing prevalence raises questions about both its position and function: the position that shadow education occupies in the educational system and the meaning students and educators attach to shadow education. In this thesis, I present four studies guided by the following overarching question: What position does shadow education take in the Dutch educational landscape and students’ school careers? Studies 1 and 2 confirmed that privileged families may use shadow education to secure an educational competitive advantage, particularly in upper secondary school. In functional terms, studies 3 and 4 imply that next to assisting underperforming students, shadow education can also provide a supportive and encouraging place to study without distractions, assisting students who repeatedly fail to comprehend teachers’ instructions, or students lacking homework support at home. In my dissertation, I describe the various roles shadow education fulfils in Dutch secondary education. I highlight that educational research, particularly research concerned with inequality of educational opportunities, needs to take account of the progressively prominent position of shadow education in the educational landscape and in students’ individual school careers.