In high-income countries, death as a consequence of recreational jumping into water from height has not been well investigated partly because it traditionally has been a covert activity within youth culture. An observational study of video recordings posted on the YouTube web site was used to gather data on the nature of jumping activity in New Zealand and Australia. An analytical framework was developed to identify site- participant- social characteristics (10 variables) and online feedback (4 variables). Of the 389 videos recorded in New Zealand (n = 210) and Australia (n = 179), 929 jumpers were observed, and rivers were the most frequently reported site of jumping activity (New Zealand 47%; Australia 35%). One fifth (20%) of the jumps in New Zealand and one third (33%) in Australia were from heights estimated to be more than 12 m. The YouTube website portraying jumps from height were visited almost half a million times (495,686 hits). Ways of reducing recreational jumping risk via targeted education interventions may be best directed at young male adults. Use of social network sites to foster safe behaviours may be an effective way to educate young people of the inherent risks of jumping from height into water.