Radicalization of vulnerable young people throughout Europe is among the latest challenges and one of the most damaging to the entire European project. Digital and social media are platforms where this threat flourishes and it is essential that the battle to suppress it is targeted at these environments. HEADS-UP is a 2-year project which aims to build the skills of front line educators and parents through in-service training and a series of simulated videos that explicitly demonstrate the on-line threats people in vulnerable positions face. This, together with a practical, user friendly set of simulation resources will enable educators to support young people more effectively by teaching them how to identify and deal with potential radicalization and grooming threats.