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Why do some covert action programs succeed, and others fail? This project argues that covert action programs are likely to succeed when the targeted polity contains a viable political coalition aligned with the covert actor. When such a coalition exists, the covert actor is essentially “pushing on an open door” and can succeed with a small-scale covert action that provides minor aid to local allies. When such a coalition does not exist, the covert actor is forced to conduct a large-scale operation to compensate for the lack of local support, which risks exposing the operation or allowing to operation to grow too unwieldy to succeed. This project aims to test this argument with a most similar case design which pairs the successful 1810 American covert action program to foment a “spontaneous revolution” in the Spanish colony of West Florida with the failed program to do the same just a year later in Spanish East Florida. The programs occur at nearly the same time, are both conducted under the James Madison administration, pursue similar strategies of promoting revolts led by elite English-speaking inhabitants of the Floridas, and are targeting the same adversaries (the Spanish colonial government). Despite these similarities, the operations vary in their results: The operation in West Florida succeeds and results in the de facto annexation of West Florida into the United States; the operation in East Florida fails, although East Florida is eventually acquired by the United States years later by treaty.