Little is known about why some children and young people are vulnerable to being groomed online, yet this has important implications for policy, practice and prevention. Therefore, the aim of this study was to identify factors contributing to a young person’s vulnerability towards online grooming. Thematic Analysis was conducted on eight interviews with young people (six females and two males) who had experienced online grooming, resulting in sexual abuse online and/or offline. The reasons why participants engaged with the offenders varied on most levels of the Bron-fenbrenner (1979) ecological model (including individual, family, community and society). The loss of family protection was found to be central in contributing to vulnerability, as is online risk taking behavior. Three victim vulnerability scenarios emerged: 1) multiple long-term risk factors, 2) trigger events and 3) online behavioral risks. In each of these scenarios, parental and family factors were very important. It is suggested that further research is needed to investigate the applicability of these scenarios to other samples. Recommendations include parent and carer communication and involvement with their children’s internet use, as well as consistent, early onset internet safety education.