This article contributes to the literature on street-connectedness and inclusive education, presenting original research findings from two Kenyan studies. Both studies aim to understand street-connected young people’s experiences of education. The first focused on transitioning from the street into education or training, to explore the challenges of making that transition. The second focused on young people who had lived on the street for extended periods of time and were still there at the time of data generation. Both studies generated significant insight into (a) education as motivating initial migrations to the street, (b) the role of fear, embarrassment, and shame in preventing young people from going (back) into formal education, and (c) how acceptance and support are key to overcoming feelings of not belonging and other challenges when transitioning from the street into school. The article provides empirical evidence that should be considered when planning inclusive education provision for street-connected young people globally.