This paper examines manumissions within the harsh and volatile culture of fourteenth-century Crete. Three large collections of notarial documents for the years 1300-1306 allow a real-time view of increased sales, decreased prices, and manumissions in the wake of the Catalan and Ottoman conquests in western Anatolia. It appears that when the price of a slave was equivalent to the wages of a hired man, slaves were freed within a fairly short time after capture. There was a variety of ways in which manumission could be accomplished, and ransoming was a business in itself. Wills from the whole century provide information about relationships, possessions, and economics, and indicate that owners often took responsibility in assuring the future stability of emancipated slaves. Cretan society was fluid enough that freed slaves of every ethnic origin were easily assimilated.