The chapter makes a theoretical and practical contribution to understanding how Housing First is successfully implemented in Finland by providing a social learning framework and showing how it operates in practice from the work of Finnish Blue Ribbon charity. Successful Housing First not only requires a supportive supply of housing and associated services such as welfare benefits provided by a mix of state, market and the third sector, sustainably overcoming homelessness requires learning why it came about and what support and emotional wellbeing is needed to overcome problems. From this perspective, addressing homelessness is an exercise in dialectical problem-solving supported by clarity over social learning processes. A framework based on Vygotsky and Engeström’s social learning, coupled with details of its practice aims to support use of a Housing First policy in other contexts and cultures. Drawing on data from the work of author Rusi (Development Director at Blue Ribbon) and Professor Stenvall’s role as Board members, who conducted 40 background interviews with Ministers, professionals in the field and homeless people, the chapter presents a detailed case study of how learning by homeless people and support staff enables success of Housing First in Finland.