This chapter critically examines the limitations of prohibition-based approaches to online safety, which have historically framed young people as passive and digital technologies as inherently dangerous. Drawing on evidence from the Headstart Kernow Digital Resilience Project, it argues for a shift towards models grounded in trauma-informed practice, ecological systems theory, and harm reduction. By reframing online harm as relational, context-dependent, and embedded within the broader microsystems and macrosystems surrounding young people, the chapter demonstrates how genuine digital resilience develops through trust, participation, and shared responsibility rather than surveillance and control. It traces the evolution of online safety practices, explains how ecosystem-based design distributes responsibility across all safeguarding actors, and shows how harm reduction offers a pragmatic, compassionate framework that aligns with what young people consistently say they need. This chapter establishes the theoretical foundations that underpin the project’s practical work in later chapters, advocating for a jurisprudence of enablement over refusal, and for approaches that prioritise understanding, empowerment, and proportionate response.