The research asks how design pedagogy can support people to reclaim freedom from within hostile environments. Drawing on the creative practices of people whose freedoms were severely restricted – including political prisoners, refugees, and enslaved people – the research considers the dialogic practices which supported them to reconfigure their boundaries of freedom. From this, a constructionist pedagogy is developed and tested with the aim of supporting asylum seekers, refugees, and vulnerable migrants in South London to reclaim freedom from within the UK’s inhumane immigration environment. Further, the pedagogy is developed and tested with a group of disabled activists who are designing protest objects for people with disabilities in a political environment where the freedom to protest is being challenged.