The integration of emerging technologies into education has reshaped teaching and policy, posing challenges for educators, especially in supporting vulnerable youth whose digital and real-world experiences increasingly overlap. As digital platforms become central to learning, teachers are expected to manage students’ on-line sexual behaviours, despite differing perceptions of technology use. This chapter explores adolescent sexting through the lens of the Theory of Reasoned Action, focusing on attitudes, subjective norms, and perceived behavioural control. These elements influence how boys perceive sexting outcomes, respond to peer and societal pressures, and assess their ability to engage or abstain. Adolescent development, marked by physical, emotional, and social changes adds complexity to sexting behaviours. Understanding sexting within this developmental and motivational framework allows for a nuanced, individualised analysis. This approach helps educators and policymakers move beyond disciplinary responses, recognising sexting as a developmental phenomenon shaped by intention, context, and technological interaction.