Tropes surrounding women’s supposed lack of intelligence are widespread in the literature of the medieval Islamic world. Authors of works of political commentary and advice often warned their elite audiences not to trust women, supporting their claims with references to a well-known narration in which the Prophet Muhammad declared women to be deficient in intelligence (naqisat al-ʿaql). Normative authors, like the famous Persian vizier Nizam al-Mulk (d. 1092), usually advocated for the absolute exclusion of women from political decision-making. Nizam al-Mulk’s views regarding the necessity of women’s isolation from decision-making roles had a long-lasting influence in the political literature of the Islamic world until the Ottoman era. Yet these attitudes were not universal, and it is possible to recover a very different approach to women’s political authority by investigating lesser-studied regions on the periphery of the Islamic world. The Yemeni jurist, poet, and chronicler ʿUmara al-Yamani (d. 1174) lived in an environment where on more than one occasion, women not only held political authority, but ruled in their own right: Sulayhid and Najahid Yemen. His History of Yemen offers a radically different view of female authority, framed by his personal experiences with the women of these two dynasties. The central figure in ʿUmara’s chronicle is the Sulayhid queen Sayyida Hurra (also known as Queen ʿArwa), who ruled Yemen first as a queen regent for her underage son, then as queen in her own right (1094–1138). ʿUmara departs from the misogynistic tropes common to many of his contemporaries, portraying Sayyida Hurra as a wise sovereign whose careful strategizing established her authority in Yemen. His account belies the notion that there existed a monolithic “Islamic” attitude toward the rule of women. By analyzing his account in comparison with that of Nizam al-Mulk, this study explores the circumstances under which female political power could be legitimized and even praised in medieval Islamic literature.