This article offers a critical reassessment of a much-neglected early Jacobean poem: Thomas Andrewe's The Unmasking of a Feminine Machiavel, a 904-line dream vision poem published in December 1604 at the end of King James I's first full year in power. The poem is modeled on a number of earlier works, including Geoffrey Chaucer's Book of the Duchess, John Lydgate's Complaint of the Black Knight, and the Mirror for Magistrates, and offers what scholars have tended to see as an autobiographical account of Andrewe's youth and misfortunes in love, as well as the part he played in the Battle of Newport (July 2, 1600). Though some of The Unmasking's intertextual features have been acknowledged before, this article seeks to fill a void in contemporary scholarship by addressing several other literary sources for Andrewe's poem and considering some of their more specific, political resonances. In so doing, this article shows that Andrewe echoes a number of contemporary authors—from Michael Drayton and Edmund Spenser to William Shakespeare and Thomas Kyd—to articulate wider tensions and anxieties over the recent peace settlement with Spain. By providing new insight into the politics behind Andrewe's appropriation of these authors, this article also aims to bring Thomas Andrewe himself into sharper focus, using his relationship to key playwrights and poets of the period (in particular, the "Jacobean Spenserians") in order to illustrate the close textual and thematic connections between dramatic and nondramatic materials and between the canon's major and minor authors and to argue for the poem's status as topical allegory published under the guise of personal complaint.