Thousands of free and self-emancipated African Americans crossed the international border in Upper Canada (present-day Ontario) in the 1830s and 1840s. But did they actually experience the legal equality and freedom from oppression they hoped to find? This chapter explores the reflections of migrants and observers on what life was actually like for African American emigrants under the British flag. It shows that while racism and educational inequity were pervasive enough in Upper Canada to slow the rate of free African American emigration to the province, the government’s ongoing commitment to protecting self-emancipated individuals and to ensuring the legal equality of black subjects ensured that Upper Canada’s reputation as a beacon of liberty steadily increased in the years preceding the 1850 Fugitive Slave Act.