As a coerced labour force living under repressive conditions, contract workers in São Tomé e Príncipe's cocoa plantations belong to a wider phenomenon of global plantation experience during the nineteenth and twentieth centuries. Flight appears as an important element of that experience and this article is an attempt to interpret the strategies of runaways in São Tomé's turbulent Great Depression years after 1930. The work set out here benefitted from a large selection of unexplored sources of the island's labour inspectorate, which can be found in the archipelago itself. Its analysis has enabled interpretation of the motives of escaping workers, and with it discussion of three principal strategic contexts of flight: the experiences of runaways who formed communities; attempts by escaped workers to hide and become part of “native” (forro) communities in rural areas or in the city of São Tomé; and the agency of workers trying to run away to subsequently renegotiate their conditions with labour inspectors or with plantation administrators sympathetic to their situation. The last part of the article attempts to locate that experience in the global history of runaways, connecting it with the types of “ecosystems of running” discussed for Atlantic slavery and later indentured labour systems.