This chapter looks at the different ways in which a free person might come to forfeit their freedom in the late antique and early Islamic Middle East. Although frowned upon and theoretically illegal, free persons might opt, due to extreme poverty or privation, to sell themselves or their family, offering their labor in return for basic sustenance. Otherwise, loss of free status might occur due to a debt default, which, if the sale of a debtor’s assets realized insufficient credit, could see them being forced to work to pay off what they owed. This solution was common in the fouth–eighth centuries, but by the ninth century it was increasingly deemed unacceptable. This chapter considers what led to this shift in legal thinking, the degree to which Islamic law continued late antique practice and the nature of this continuity.