Khaqani refers to his ascendant sign nine times throughout his poetry, yet he inconsistently identifies it as either Cancer or Leo. Most commentators have regarded Leo as his true ascendant, interpreting his references to Cancer as purely metaphorical: since the crab (Cancer) moves backward and obliquely, they suggest that Khaqani invoked it symbolically rather than astrologically, without any connection to his actual horoscope. This article challenges that assumption and argues that a poet such as Khaqani—renowned for his extensive and precise knowledge of astronomy and astrology, could not have erred on a matter as fundamental as the ascendant, which forms the basis of numerous calculations in classical astrology. By dating several of the poems in which he mentions his ascendant, we demonstrate that Khaqani initially believed his ascendant to be Cancer, but later discovered that it was in fact Leo. In tracing this intellectual and poetic transformation, we further analyze his opposition to the astrological predictions surrounding the great conjunction (qirān) of 582 AH. This analysis reveals the central role of the concept of qirān-i mustarqa (“concealed conjunction”) in shaping Khaqani’s rejection of those forecasts. Overall, the study highlights the poet’s sophisticated engagement with astrological discourse and his evolving interpretation of celestial signs within the broader context of medieval Persian intellectual culture.