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The poetry of Virgil famously inspires a plethora of antithetical interpretations. In particular, the Eclogues have instigated unending dispute about Virgil’s intentions in employing the pastoral mode and his opinion of the pastoral world itself. Does Virgil approve of the bucolic ideal, or does he denounce it? Scholars abound on both sides of the debate. In an effort to decipher Virgil's true understanding of the pastoral world and its poetry, in this paper I examine Virgil’s use of the quintessential pastoral trope: umbra. On a first reading of the Eclogues, one observes Virgil's frequent use of the classic bucolic image of a shepherd singing in the cool shade of a tree or cave. This picture recurs throughout the poems with slight variations, but each time Virgil seems to portray umbra in a positive light, thus apparently endorsing the pastoral ideal. Upon looking more closely, however, one notices other uses of the word umbra, instances in which Virgil introduces a much more pessimistic mood. More than once he incorporates umbra in descriptions of nightfall’s chill shadows cast across the land after sunset. Such ominous uses of umbra complicate the reader's understanding of Virgil's intentions. Why does he introduce a sense of foreboding with the same word that epitomizes the simplicity and beauty of the pastoral world? I argue that Virgil’s two-edged use of umbra demonstrates his view of the pastoral itself. While he refuses to reject the bucolic ideal, allowing it to retain a certain peaceful grace, he simultaneously hints at a perilous aspect of pastoral life. Through his equivocal use of umbra, Virgil reveals his nuanced understanding of the bucolic world and its literature. As Christine Perkell writes, "This lack of clarity, this real impossibility of uncomplicated and definitive moral judgment, is Virgil's hallmark" (181). His reader must take into account both Virgil’s positive and his negative portrayals of the pastoral trope of umbra in order to fully recognize Virgil's well-rounded, complex view of the bucolic as a fascinating but mysterious world.