This guide tells the story of a successful collaboration between The City Literary Institute and homelessness agencies to create an arts-based learning program for homeless people in central London. It identifies guidelines and good practice to stimulate similar work in other locations with problems of homelessness and rough sleeping. The guide is intended for managers in learning providers, homelessness agencies, and statutory and voluntary funders and for front-line teachers and workers with homeless people. Following an introduction and description of the Rolling Shelter project (RSP), a section identifies these issues managers must address in developing programs: building partnerships, developing provision, selecting a curriculum and teachers, triggering learner motivation, progression, and program sustainability and review. They are set out in a checklist, then expanded and illustrated with examples and quotations from RSP. Brief case studies follow. The next section suggests practice likely to produce successful learning for homeless learners: understanding the client group, working together, offering learners flexibility and choice, providing structures and outcomes, recording achievement, and encouraging progression. The key points are summarized in a checklist, then illustrated with quotations and case studies from RSP. Appendixes include lists of 8 publications and 16 useful websites and sample workshop forms. (YLB)