This paper examines the challenges of digital transformation within the charity sector by exploring the ways in which the digital divide affects young service users and staff. It provides an overview of the challenges and lessons learnt across three interrelated projects which were undertaken in partnership with the Refugee Council (RC), the leading UK charity supporting refugees. The key challenges to digital equity for young refugee clients pertain to their material and living conditions, digital literacy, and quality of personal relationships. In addition to technical obstacles, charity staff working with young people in difficult circumstances find challenging to set and maintain boundaries and to manage personal and interpersonal lives when working online. Two main organisational challenges are identified: fundraising and data protection. Charities need guidance on what services can be digitised successfully and need support with grounding their digitalisation in the above specific needs of the clients. In conclusion, a digital equitable society will be successful not only if charities adapt, but if digitalisation strategies also adapt to the specific needs and realities of the charity sector and to individuals who are often at the margins of digital innovations. It needs to be a two-way process.