The reigns of Boran and Azarmidokht, two Sasanian queen regnants, reflect a crisis of legitimacy and a transformation in power structures during the final years of the Sasanian Empire. This study addresses two questions: (1) How have Islamic historians portrayed Boran and Azarmidokht? (2) What common features regarding these queens emerge across historical narratives? An analysis of accounts by historians such as al-Tabari, Bal'ami, al-Tha'alibi, Ibn al-Athir, al-Ya‘qubi, al-Dinawari, and al-Mas‘udi shows that portrayals of Boran as wise and just, and Azarmidokht as beautiful yet militant, are not mere reflections of individual traits but parts of a broader discourse on legitimacy, gender, and historical representation. These reports, through themes of crisis, exception, and failure, temporarily legitimize female rule as an emergency measure while depicting the demise of the patriarchal order and the political decline of the Sasanian structure. The findings reveal that despite differences, a shared representational pattern governs their depictions, enabling analysis of power, gender, and memory mechanisms. By highlighting dominant discourses and employing comparative analysis, this study offers a critical, multilayered reading of the reigns of Boran and Azarmidokht and opens new perspectives for future research in historiography and political discourse.