In this chapter that bit of troubling and prying open is directed toward a rethinking of youth transition and the role of schools in that particular form of ‘becoming.’ Teenage mothers appear as they, too, are ‘known’ to be trouble makers: the ‘teenage mother’ signifier is, by default, a negative one. As Sara found, ‘teenage mother’ as a signifier doesn’t rest easily alongside ‘school girl’ as a signifier. It is this assemblage of teenager+parent+school student – a gathering in which I too was once involved (Kamp and Kelly 2014) – that is the focus of this chapter. I engage with my prying by plugging into the academic literature and empirical research undertaken in Australia on the becomings of those young people, most commonly young woman, who, through their ‘becomingparent’ (for whatever reason) form, or reform, their connections with the education system. In this becoming they create assemblages that can be profoundly troubling for schools.