This paper seeks to contribute to this line of research by examining America’s first occupation of Haiti from 1915–1934. As with the occupations of Cuba, the Philippines, Puerto Rico, and the Dominican Republic, the U.S. installed a military government in Haiti. American military officials had virtually complete control over the operations of a parallel, client Haitian government. Unlike other occupations, however, this story begins, ends, and is shot-through with educational concerns. It begins with lessons about Haiti taken by the Woodrow Wilson administration shortly before the U.S. invasion in 1915. The consultants they turned to for advice — particularly captains of the American financial industry with large investments in Haiti — significantly coloured the way they approached the country’s problems and potential. The story ends with Haitian protests over U.S. imposed educational reforms, protests that spread, intensified, and led to the end of the American occupation in 1934.