The book of Kalīla wa-Dimna has been apprehended in variegated ways: as an originally Indian book, one of the first Arabic adab works, as a mirror for princes and a collection of fables. In spite of varying construals of Kalīla wa-Dimna, until recently there is one shared denominator among modern textual scholarship: it is a fictional narrative. Although such interpretation seems intuitive to a modern reader, it is questionable when taking a historical perspective. Since there is no precise equivalent of "fictionality" in the classical context, the concept can neither be naturally assumed, nor be approached as a single unitary notion that we have to simply translate and then seek to find by identifying “signals” or “signposts” of fiction/fictionality. Building upon approaches that attempt to reconstruct premodern modes of understanding and using textual production, in this article, I suggests to conceptualize fictionality as a hermeneutical category which encompasses different perspectives of what about and in a text is fictional. After shedding light on the problem of fiction/-ality in Arabic before modernity and expounding the hermeneutics of fictionality, I will draw from three types of references to Kalīla wa-Dimna in the Arabic tradition between 750 and 1300 AD: first, the notion of practical wisdom and its independence from demonstrable referentiality; second, the problem of reliable transmission; third, the notion of parables and invented content.