In 1975, Indonesian forces overran East Timor, just days after it declared independence from Portugal. Canadian officials knew the invasion was coming and endorsed Indonesian rule in the ensuing occupation. Challenge the Strong Wind recounts the evolution of Canadian government policy toward East Timor from 1975 to its 1999 independence vote. During this time, Canadian civil society groups and NGOs worked in support of Timorese independence activists by promoting an alternative Canadian foreign policy that focused on self-determination and human rights. After following the lead of key pro-Indonesian allies in the 1970s and ’80s, Ottawa eventually yielded to pressure from these NGOs and pushed like-minded countries to join it in supporting Timorese self-rule. David Webster draws on previously untapped government and non-government archival sources to demonstrate that a clear-eyed view of international history must include both state and non-state perspectives. The East Timor conflict serves as a model of multilevel dialogue, citizen diplomacy, and novel approaches to resolving complex disputes.