Evidence suggests equine-assisted activities may provide psychological benefits to young people “at-risk.” Results are presented from an equine program among 14- to 16-year-old children (N = 7), mostly boys (N = 6), attending a non-traditional flexi-school in Australia. Thematic analyses were undertaken on observations by facilitators, researchers, and a school teacher, and interviews with a school teacher. Key themes suggest that program participants benefited from positive engagement, social connectedness, and increased confidence, relationships, and attachment. Mechanisms were identified as a desire and an ability to connect with the horse and a positive environment. The social context of the equine program contrasts with other contexts in these young people’s lives, which allowed them to engage through more positive relational, affectionate behavior. For the boys, positive rather than damaging masculine behavior was displayed. Furthermore, the compatible student-environment interactions provide a backdrop which makes other positive changes possible.