This paper attempts to interpret the iconography of a seventeenth-century manuscript painting from India at the San Diego Museum of Art. It considers the iconography of "Alexander in a chinar tree, greets two sages and their retainers" from an Iskandarnama manuscript, dated circa 1610, by deciphering the symbolic significance of the various figures depicted. The function of such figures as the herder and his cattle in the upper section of the painting, or the plane tree with its multi-colored leaves, and the smaller blossoming tree in its lower half, and other details, are traced back to the germination of such iconographic configurations more than a century earlier at the workshops of the last Timurid ruler in Herat. It was then that Persianate manuscript illustrations began to include figure-types that seem to have little or no connection to the narrative of the accompanying text. Such extra-textual depictions disturb the transparency and cohesiveness of the composition and have never been satisfactorily accounted for, although they abound in post-fifteenth century paintings from Iran, Central Asia, and Mughal India. The figures in the "Alexander in a chinar tree" are traced back to their iconographic and symbolic origins, when the intertextual discourse of Sufism--and above all its metaphors for remembrance of and ultimate union with the Divine-- already popularized by the Persian and Indo-Muslim poets, finally penetrated the art of figural manuscript painting. Through textual analysis of Sufi works--or works whose narrative could be read allegorically as such--together with the iconography of a number of key manuscript paintings that illustrate passages from these works, the paper will demonstrate that even as the illustration of the allegorical narrative forms a normative relation with the literal meaning of the accompanying passage of Iskandarnama--which serves as the textual vehicle--the referents for the other heretofore enigmatic figures within the painting can be traced back to the dominant Sufi discourse of Persianate culture in the fifteenth century. By the beginning of the seventeenth century, many such figure-types retained at least some traces of their original symbolic mystical significance, while others became associated with altogether new referents or were reduced to mere ornaments. The analysis of this painting made during early seventeenth century in the Indian subcontinent will therefore engage the iconology of manuscript painting in the eastern Islamic world in a broad sense.