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At St. Sabas, John devoted his time to anti-heretical writing. Given his firsthand knowledge of Islam, it is not surprising that he turned his attention to defending the Christian faith against Muslim teaching, which he considered to be a kind of Christian heresy. His polemical work for Christians, "Against the Ishmaelite Heresy," was, in keeping with the genre, intentionally derogatory in tone—a sort of "anti-creed" that explained, "This is what we do not believe, and here's why … "

John's familiarity with Islam is evident throughout the work; he cites numerous details of Muslim faith and practice and quotes ten different Qur'anic verses. But his tone is not conciliatory, and he makes statements such as "Mohammed wrote many ridiculous books" and "Mohammed said: 'Oh by the way, God has commanded me to take your wife'"—clearly not an approach that promotes constructive engagement with Muslims.

But John was a product of his times, and he reflects a noble, if not always nuanced, commitment to Christian orthodoxy. His words represent the first substantive Christian engagement with the Muslim community in writing. In both good and bad ways, he set the tone for future Christian-Muslim interactions.

Like John of Damascus, Patriarch Timothy I grew up as a Christian under Muslim rule. Born 50 years after John and 500 miles from Damascus, he came of age under the second great Muslim dynasty, the Abbasids of Baghdad. Timothy succeeded his uncle as bishop of the Assyrian Church, sometimes referred to as the Nestorian Church. In this role, he oversaw churches and missionaries as far away as China. (The rest of Christendom considered the Assyrian Christians heretical at that time, though this may have had more to do with politics than theology.)

As a Syriac-speaking Christian leader educated in the Greek classics and living among Arab Muslims, Timothy was ideally situated to be a bridge between the cultures and ideas of the classical West, the Assyrian Church, and the Muslim community. He developed the intellectual and diplomatic skills that would later distinguish him as the most nuanced of the early Christian leaders in his interactions with Muslims.

In 781, Timothy participated in a celebrated debate with the third Abbasid caliph, al-Mahdi. Given the respectful tone of both men, it is perhaps more appropriate to call the exchange a dialogue. Timothy's words are a model of how to maintain Christian orthodoxy while accommodating the message to Muslim perspectives and experiences.

Timothy later wrote of their exchange: "After I had paid to him my usual respects as King of Kings [the appropriate title of address to the caliph at the time] he began to address me and converse with me not in a harsh and haughty tone, since harshness and haughtiness are remote from his soul, but in a sweet and benevolent way." The caliph inquired about the Trinity, "If He is one, He is not three; and if He is three, He is not one; what is this contradiction?"

Speaking of the king as "his exalted Majesty," and addressing him with affection and respect, Timothy replied: "The sun is also one, O our victorious King, in its spheric globe, its light and its heat, and the very same sun is also three, one sun in three powers. In the same way the soul has the powers of reason and intelligence, and the very same soul is one in one thing and three in another thing. In the same way also a piece of three gold denarii, is called one and three, one in its gold that is to say in its nature, and three in its persons that is to say in the number of denarii. The fact that the above objects are one does not contradict and annul the other fact—that they are also three, and the fact that they are three does not contradict and annul the fact that they are also one."

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