This paper tackles what is arguably the most pervasive and pressing educational issue confronting affluent Western countries – the disengagement, disconnection and tragic displacement from schooling of increasing numbers of young people, mostly those from backgrounds of disadvantage. Despite enormous policy efforts, this ‘problem’ is proving impossible to dislodge from within the existing educational policy paradigm that appears to be exacerbating the problem. This paper explores theoretically and practically what alternative attempts might look like that start from within the lives and experiences of those most affected, young people as well as their teachers, and it explores what some research ‘portraits’ look like from ‘inside’ the existential realities of these complexities. Employing the heuristics of ‘new mobilities’, the paper looks at some alternative ways of locating ‘new social spaces’ from which to re-engage and re-connect these young people with learning, and with some effect. The paper is sanguine about the extensive work yet to be done, and in this regard it proffers some thoughts on the unfinished business of what it terms a ‘critical pedagogy of engagement’.