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This essay examines the language of an expatriate community as found in letters and petitions written by African Americans who migrated to Sierra Leone by way of Nova Scotia in 1792. These documents provide some of the earliest first-hand evidence of African American English and contribute to debates about the history of that variety. The paper compares selected grammatical features in that variety to modern-day African Nova Scotian English for insights to the history of African American English and develops a case for the principled use of manuscript documents for reconstructing earlier stages of colloquial English.