There is increasing recognition of the role eHealth will play in the effective and efficient delivery of healthcare. This research challenges the assumption that students enter university as digital natives, able to confidently and competently adapt their use of information and communication technology (ICT) to new contexts. This study explored health sciences students' preparedness for working, and leading change, in eHealth-enabled environments. Using a cross-sectional study design, 420 undergraduate and postgraduate students participated in an online survey investigating their understanding of and attitude towards eHealth, frequency of online activities and software usage, confidence learning and using ICTs, and perceived learning needs. Although students reported that they regularly engaged with a wide range of online activities and software and were confident learning new ICT skills especially where they have sufficient time or support, their understanding of eHealth was uncertain or limited. Poor understanding of and difficulty translating skills learned in personal contexts to the professional context may impair graduates ability to confidently engage in the eHealth-enabled workplace. These results suggest educators need to scaffold the learning experience to ensure students build on their ICT knowledge to transfer this to their future workplaces.