Digital lifelong learning and more specifically digital peer learning (DPL) can play a major role to foster transformative agency in professions and occupations which are critically positioned for responding to acute societal needs. Yet so far, no published studies seem to have focused on this. This article aims at filling this gap with the help of a study in which online workshops and web forums were created for supporting homelessness practitioners in Finland to share and discuss scattered practical innovations and to generate advanced solutions to problems in their work. By these means, the study also generated data to see if transformative agency takes place among these professionals by means of DPL, how this happens, and with what results for the critical field of homelessness work. This study opens up a new agenda for research and development in lifelong learning in a digital era.