Youth today suffer from many socio-economic problems and struggle to operate in the current economic environment. Wellbeing service provision to youth@risk is inadequate to deal with the complexities of societal challenges which are amplified by the fast technology advances in a continuously changing environment. This paper aims to consider the provision of online counselling to enhance current face-to-face services from the provider’s perspective. The case of a volunteer-based online counselling service that has been in operation since 2010 is considered to establish the aspects that influence this type pf service. Related literature was reviewed to determine the issues reported from current studies and a taxonomy of digital services was used to analyse the service objectives of the service provider. Data collected from sessions with the facilitators and observations of a chat session was analysed to establish their experience of online counselling. The findings were interpreted to answer the research question. The contribution of this paper is in response to the many appeals for more empirical research on real cases. It can be concluded that an online counselling service is a viable extension of face-to-face counselling but more research is needed to understand its benefit to the clients and the ability to ensure a sustained service, especially in developing contexts.