This chapter examines how online safety for young people with Special Educational Needs and Disabilities (SEND) is often oversimplified through one-size-fits-all resources and restrictive safeguarding practices. Drawing on insights from the Headstart Kernow Digital Resilience Project, it highlights the complexity and diversity within the SEND population, where digital spaces can be both vital for communication, inclusion, and identity development, and simultaneously a source of heightened risk. Rather than framing SEND learners as inherently vulnerable, the chapter argues for rights-based, relational, and contextual approaches grounded in ecological systems thinking and harm reduction principles. Through stakeholder feedback from young people, educators, and parents, it explores tensions between empowerment and protection, emphasising the importance of trusted relationships, adaptive teaching, and collaboration across the microsystem. The chapter introduces the Headstart SEND Digital Resilience resource, designed to support adults in tailoring guidance to individual needs, strengthening disclosure pathways, and enabling participation without fear-based restrictions. It concludes that meaningful safeguarding for SEND young people must prioritise autonomy, adaptability, and dignity-recognising them as active rights-holders whose digital lives thrive through confidence and connection rather than control.