While pedagogy is predominantly viewed from the perspective of classroom instruction, educators worldwide invariably play a critical pastoral role of shaping the personal development of their students and nurturing in them life skills. With the avid use of participatory media by young people in peer interaction, educators need to be aware of the attendant risks and opportunities so that they may offer counsel and render appropriate advice. To this end, through interviews with 36 Singaporean male juvenile delinquents and youths-at-risk, this study explores how these youths utilise participatory media in their peer interaction. The findings indicate that for this vulnerable youth population, participatory media such as social networking sites can become a platform through which they are unwittingly drawn into criminal behaviour and post-rehabilitation, participatory media may offer an insidious route to recidivism. Participatory media complicates peer interaction by presenting risk factors such as network transparency, negative peer modelling, network seepage and network persistence, all of which have implications for these youths sliding further into delinquency and criminal activity. This article concludes with recommendations on the strategies which youths-at-risk can employ to avoid the risks of participatory media. (Contains 2 tables and 1 note.)