The third ʿAbbasid caliph, al-Mahdī (r. 775–785), held a complex relationship with religion and theology. On the one hand, he made strives to heal divisions between the ʿAbbasids and ʿAlids. On the other hand, he promoted orthodoxy by suppressing, and at times even attempting to eradicate, heresy. As al-Mahdī worked to promote unity within Islam while oppressing heresy, how did Christians view his rule in Baghdad? While al-Ṭabarī (839–923) recorded a detailed account al-Mahdī’s reign, he gave few glimpses into his interactions with Christians in Baghdad. Further, how can Christian sources inform the modern study of the early ʿAbbasid period? In this paper, I argue that although Islamic sources presented al-Mahdī as a zealous defender of orthodoxy, Christians from Baghdad presented the caliph as a benevolent and just ruler in pursuit of truth. Two Christian sources in particular—the Disputation with the Caliph of Timothy I, Patriarch of the Church of the East (ca. 740–823) and the Martyrdom of Habo, the Perfumer from Baghdad—depicted events in Baghdad during his reign. In Timothy’s Disputation, which appears to preserve some elements of a verifiable dialogue between Timothy and al-Mahdī, the caliph is presented as a just ruler genuinely in pursuit of truth. While the Syriac version (published by Alphonse Mingana) and early Arabic translation (published by Samir Khalil Samir and Wafik Nasry) of this text hold significant differences, they both contain these positive depictions of al-Mahdī. The Martyrdom of Habo is an eighth-century Georgian text which recounted the conversion of Habo, a Muslim perfumer from Baghdad during the reign of al-Mahdī. The perfumer resolutely faced martyrdom under the reign of al-Mahdī’s son Musa al-Hādī (r. 785–786). Although a hagiographical and embellished account, this work praised the rule of al-Mahdī even while showing animosity to lower-level Muslim magistrates. This study seeks to inform broader discussions on religious tolerance and the boundaries between Christianity and Islam during the early ʿAbbasid era. In this it seeks to contribute to foundations established by Robert Hoyland (Seeing Islam as Others Saw It), Michael Philip Penn (Envisioning Islam), and Jack Tannous (The Making of the Medieval Middle East), adding that these two sources can help to show the multifaceted nature of early Muslim-Christian relationships.