The concept of educational questions has often been taken up topically, or as a related component to topics within philosophy of education. The rabbit hole approach provides a new perspective for attempting to discover the characteristics of educational questions and to engage with six authors, Biestra, Bingham, LeGrange, Andreotti, Saeverot and Snir seemingly, six conceptions of educational questions. Schulz suggests that the rabbit hole can operate as iterative, exhaustive, or associative. This paper traces the author's exhaustive and associative "rabbit hole" via questioning and inquiry to reveal the ways in which various conceptions of one single concept are presented when philosophy of education students explore educational questions within the field.