Critiques of the poetics associated with Tāza Gū’ī (Speaking Afresh), which spread in Persian poetry starting in the sixteenth century, often focus on the alleged difficulty of poetry composed in this mode. Related critiques are that the difficulty of Speaking Afresh poetry is excessive, unnecessary, and often unrewarding: that one may struggle through a poem, only to find that it has, in the end, no clear or definite meaning. Shawkat Bukhari (d. 1695) is one of the poets whom critics of the difficulty of Speaking Afresh may cite as a particularly difficult poet, one said to have composed poetry in the notorious ṭarz-i khayāl (manner of the imagination), as opposed to the earlier and less obscure ṭarz-i tams̱īl (manner of exemplification). A growing body of modern scholarship has worked to demonstrate how the poetics of Speaking Afresh functioned on its own terms, including by arguing against the notion of difficulty (or related concepts) as necessarily indicative of poetic weakness or decline. This paper aims to both draw on and contribute to this recent scholarly work by raising the question: what are the explicit and implicit understandings of meaning-making in Shawkat’s poetic collection (dīvan), and how might these resonate with a poetics that eludes fixed, straightforward, and unambiguous readings? In relation to Shawkat’s dīvan, I note connections to two broader emphases in Speaking Afresh poetry. The first is the poetic practice of maintaining multivalences within a single verse, often by retaining the literal meanings of metaphors alongside their figurative meanings; due to the resultant ambiguity, this practice may be subsumed under the category of difficulty. The second broader emphasis of interest is a concern with the question of the relationship between unchanging divine unity (vaḥdat) and variable worldly multiplicity (kis̱rat). While these two emphases may seem separate, I argue that the cultivation of multivalences in Shawkat’s dīvan resonates with and in fact models a certain understanding of the need to be comprehensive of worldly multiplicity, as a form of orientation toward unity.