This paper analyzes early Islamic historical accounts of the Sasanian monarch Khusraw II Parviz’s (d. 628 CE) multiple dealings with the Arab tribes and states of the Arabian peninsula and Iraq, including the Lakhmids of Hira, the Banu Tayyi’, and towards the end of his reign, the embryonic Muslim community. The sources under consideration include the works of Tabari, Bel‘ami, Mas‘udi, Yaq‘ubi, Dinawari, Tha‘alibi, Ibn 'Abd Rabbihi, and Abu’l-Faraj al-Isfahani. These chroniclers’ reports of Parviz’s treatment of and meetings with the Arabs bare telltale signs of anachronistic embellishment. They highlight conspicuous examples of the Iranian sovereign’s hubris, decadence, and disdain for Arab culture, which contrast starkly with illustrations of the Arabs as embodying idealistic values and characteristics associated with the rugged lifestyle and traditions of the Bedouin. My paper asks how contemporaneous attitudes and biases of the early Islamic world have been projected onto the historical portrayal of Parviz in the context of his dealings with the Arabs, and to what end. I argue that in the Islamic sources, Parviz and the Arabs he encounters serve as anachronistic protagonists of the Shu‘ubiyya debate, which pitted the proponents of Iranian civilization (the Shu‘ubis) against the defenders of the Arab cultural heritage (the anti-Shu‘ubis). This controversy reached its height between the 8th and 10th centuries in the urban centers of Iraq and Iran. By emphasizing his predilection for luxury, oppression, his haughty disregard of the Arabs, and finally his self-righteous rejection of the message of the Prophet, Parviz is made, in these highly formulaic accounts, to exemplify the anti-Shu‘ubis’ defaming critiques of the culture and imperial legacy of Iran. In contrast, by demonstrating their munificence, steadfastness, and eloquence in the face of the Iranian sovereign, the Arabs whom Parviz comes across in the course of his reign conform to ideals of Arab culture circulated among the nostalgic defenders of the Arab tradition. Furthermore, I argue that the reports of these encounters form part of a broader didactic narrative contained within the Islamic historical tradition explaining the rise of the Arabs under the banner of Islam, and the fall of the Sasanian dynasty. In this way, evocative themes, symbols, and arguments drawn from the Shu‘ubiyya controversy that have been projected onto these historical adversaries serve to both foreshadow and legitimize the Arabs’ conquest of Iran.