While many schools have gravitated away from an emphasis on 'zero tolerance' discipline, embracing a range of 'restorative practices' (RP), only a handful of empirical studies have examined how RP have been received by educators. Moreover, frameworks which embrace RP in the classroom often neglect newer forms of online-mediated conflict and harm (e.g., cyberbullying, 'sexting'). The current study, drawing on 77 qualitative interviews with Canadian pre-service and practicing educators, examines their responses regarding the effectiveness of RP in response to online conflict and harm. Challenges include educator emotional burnout, pressures on popular teachers to run RP, and the need for resources and administrative support in RP or an external mediator. These challenges, we argue, are difficult to overcome without a whole school framework that helps to instill cultural commitments attending to the wider goal of repairing harm situated at the level of a school's community.