Sierra Leone has a long history of community philanthropy. However, not much is known about citizens’ pattern of giving, the recipients of gifts and the sociopolitical and economic factors that shape the trajectories of community philanthropy in the country. Drawing on field-based research undertaken in Bo district in the South, Bombali district in the North, Freetown in the Western Area and secondary data, this report analyses Sierra Leone’s community philanthropy landscape. It identifies two broad and enduring patterns of community philanthropy – associational philanthropy and individual philanthropy. The report argues that while the different forms that community philanthropy assumes at any given time are embedded in sociocultural expressions of kindness and mutual dependence, they are also fundamental adaptation strategies to evolving socio-economic shocks and structures that shape people’s lives and resilience, whether in the colonial or postcolonial era. These shocks have included adjusting to colonial rule’s policy of “divide and rule” and post-independence state failure – leading to underdevelopment, civil war and complex emergencies. The report reveals striking patterns of continuity and change in Sierra Leone’s philanthropic landscape, with a progressive decline in public trust in state-led philanthropic schemes, especially during national emergences or crises.