Most Sunnī scholars unequivocally exempt poor dhimmīs (mostly Christians and Jews under Muslim rule) from the duty to pay the Qur ān-imposed poll tax. Shāfi ī scholars, however, hold two conflicting opinions, one that exempts the poor and another that does not. This article examines the reality of destitute Jews living in Egypt and Syria under the Ayyubid regime in order to determine which of the two conflicting Shāfi ī rulings was applied in practice. Drawing on Geniza documents and literary sources, I argue that in the Ayyubid period no exemptions were offered to the poor whatsoever. This taxation policy, in my view, may reflect not an arbitrary choice made by local Ayyubid tax officials, but a conscious decision made by the Ayyubid rulers and the leading contemporary Shāfi ī scholars. The Ayyubids most likely appealed to the Shāfi ī religious authorities, pressing them to adopt the more stringent opinion, which would allow authorities to refrain from exempting the poor.