Digital technologies are being used as part of international efforts to revolutionize healthcare in order to meet increasing demands such as the rising burden of chronic disease and ageing populations. In Scotland there is a government push towards a national service (Living It Up) as a single point of reference where citizens can access information, products and services to support their health and wellbeing. The aim of the study is to examine implementation issues including the challenges or facilitators which can help to sustain this intervention. We gathered data in three ways: a) participant observation to gain an understanding of LiU (N=16); b) in-depth interviews (N=21) with stakeholders involved in the process; and c) analysis of documentary evidence about the progress of the implementation (N=45). Barriers included the need to “work at risk” due to delays in financing, inadequate infrastructure and skill-set deficiencies, whilst facilitators included trusted relationships, champions and a push towards normalisation. The findings suggest that a Scottish ehealth service is achievable but identifies key considerations for future large scale initiatives.