Online outsourcing (OO) involves global outsourcing of tasks from clients to freelancers via platforms such as Upwork, Guru, Freelancer and Fiverr. Governments and donor agencies in several developing countries are currently starting OO training initiatives to enable access to digital livelihoods for marginalised groups such as youth and women. However, little is known about the impact of these initiatives and in response this paper reports on empirical research into OO projects in Pakistan. Supported by the sustainable livelihoods framework, the analysis shows a context of politico-economic vulnerability. Many freelancers do not succeed but some entrepreneurial individuals motivated by earnings potential are able to generate sufficient livelihoods. Contrary to an image of deinstitutionalised work, this form of digital labour involves a substantial institutional ecosystem. This implies a broad range of stakeholders including the platforms, formal interventions from policymakers and development agencies and the creation of informal support mechanisms.