Compiled in the seventeenth century, Shihāb al-Dīn al-Khafājī’s (d. 1069/1659) Rayḥānat al-alibbāʾ wa zahrat al-ḥayāt al-dunyā became something of an instant classic throughout the Islamic world. The work reached well beyond its Egyptian provenance to find audience everywhere from the Ottoman Balkans to Mughal India. More than a mere record of his contemporaries’ poetry, al-Khafāji’s Rayḥānat al-alibbāʾ is a manual for style and poetics, a work of literary criticism, an ego-document betraying its author’s intellectual commitments, and a snapshot of the classical Arabic canon at a specific time and place. While little studied today (and almost never taught), the Rayḥānat al-alibbāʾ was one of the most copied Arabic literary works in the centuries leading up to the Nahḍa. Even during the boom of printing during the nineteenth century, when the classical Arabic canon as we know it today supposedly began to take form, the Rayḥānat al-alibbāʾ was thrice printed in Egypt (1273/1853, 1294/1877, 1306/1888) alongside near-simultaneous manuscript witnesses, though it would not see publication again until Muḥammad Ḥulw’s edition in 1967. In this paper I explore how this exemplar of late adab profited off its Ottoman-era popularity to be repeatedly selected for print publication during an age of “rediscovering of the Islamic classics.” I then investigate how the Rayḥānat al-alibbāʾ lost its cachet among scholars, printers, and readers, and ultimately failed to gain inclusion into the modern construction of the classical Arabic canon. With an interest in the parallels between literary and intellectual history, I explore the missed connections or simultaneous and incongruous trajectories of the modern construction of the classical Arabic canon. What factors granted al-Khafājī and his anthology the designation of modern or canonical print is often seen to bestow? Are canonicity and modernity even coextensive within literary history? I hope to show that the classical Arabic canon is a perpetually shifting collection of texts and textual practices no more authoritative (or modern) in the late nineteenth century than in the seventeenth. Rounding out my paper, I will posit that recent, ever accelerating scholarship on the post-classical Arabic literary tradition is yet another stage of refashioning the classical Arabic canon, one we must be deliberate and transparent about as we continue to produce it.