Free women of colour in the Southern Caribbean in the eighteenth and nineteenth centuries succeeded not only as ‘madams or mistresses’ but also as entrepreneurs and matriarchs. The colonial archive, as reexamined by Kit Candlin and Cassandra Pybus, reveals new facets to the dynamics of gender, wealth, power, and race in the ‘Revolutionary Atlantic’. Enterprising Women draws on an impressive selection of wills, tax records, slave registers, letters, memoirs, petitions, and court proceedings to retell the story of successful women of colour in the ‘ceded islands’ of the British South Caribbean between 1763 and 1840. Candlin and Pybus re-read the documents that have served to tell the reductive story of a few illegitimate interlopers in a society strictly divided between a white plantation- and slave-owning elite and an enslaved black workforce. They also share previously ignored or unknown archival material that supports the story of ‘enterprising women’, savvy businesspeople, careful matchmakers, and effective brokers of the means of power in a colonial world in flux. These women emerge not as the unsung heroines of the colonial Caribbean, but as actors in a complex set of power relations where race, class, gender, and legitimacy are so many intersecting and transecting lines in a kaleidoscopic world.