Educators have an increasingly important role in supporting children with disabilities to connect with and through the Internet. Children with disabilities encounter more risks in connected environments than their peers. These risk experiences are likely to escalate quicker and have more serious impacts for children with disabilities. Yet this group receive less support from educators in their connected lives. Taking this juxtaposition as our starting point, we used purposive sampling to recruit a range of educators who support children with disabilities aged 8-16 years. We used online semi-structured interviews to collect data from 30 educational professionals over a 5-month period (May-September 2021). Our thematic discourse analysis identified three main themes depicting how educators experience and make sense of the connected lives of children with disabilities: fortresses and frontiers, patrolling the borders and getting comfortable with the uncomfortable. Our analysis illustrates how educators make use of widely available binary talk related to ‘online’ risks to create simplified versions of safe (fortress) and unsafe (frontier) spaces. This meant educators frequently positioned their role as restricting access to unsafe spaces. Alternative mobilisations enabled educators to reconstruct short-term online risk experiences as experiential learning opportunities in the lifelong pursuit of supporting children with disabilities to build and show digital resilience. We conclude by illustrating how educators should embrace the increasingly connected lives of children with disabilities through a digital resilience lens, becoming exploration guides not simply restrictive protectors.