Middle schooling can sometimes be a turbulent time for adolescent and pre-adolescent learners, as they position themselves in the world. This is evidenced by behaviours that can challenge mainstream schools, thus alternative models of schooling are sometimes used to re-connect the learners. Of particular focus is the emotional wellbeing of these 'at-risk' students whose experiences are often shaped by relational factors. Drawing on the Eccles et al. (1983) expectancy-value theory, this study investigated the views of 'at-risk' students involved in three different models of alternative education in Adelaide, South Australia: an alternative school, alternative program and alternative placement. The study adopted a mixed methods design with twelve students, aged seven to thirteen (m = 11.75 years), through both survey and interview. Students revealed that their socialisers, particularly teachers and peers, strongly influence their emotional wellbeing and valuing of education. These findings are significant in shaping the ways in which teachers work, and support the emotional wellbeing of, students 'at risk' of educational failure and questions whether alternative models of schooling re-connect or dis-connect learners in the middle years.