This essay argues that John Milton and Paradise Lost were embroiled in a century-long dialogue about gender that positions his epic alongside writers in the early seventeenth-century “anti-feminist” debate (Rachel Speght and Ester Sowernam), women poets from the early and late seventeenth century (Aemilia Lanyer and Mary Chudleigh), and a major female political and educational theorist (Mary Astell). Surrounded by women writers who engage narratives of the Fall, issues of gendered culpability, and even representations of Christ’s Passion and redemption, Milton’s Paradise Lost internalizes lines of inquiry posed by early seventeenth-century texts authored by women. This essay focuses mainly on how the works of Speght and Sowernam are explored through Paradise Lost and then further interrogated and reworked in the writings of Mary Astell. In their early seventeenth-century responses to Joseph Swetnam’s The Arraignment of Lewd … Women (1615), Ester Sowernam in Ester Hath Hanged Haman (1617) and then Rachel Speght in her “Dreame” vision poem within Mortalities Memorandum (1621) offer a portrait of a solitary Eve in search of knowledge who disrupts the implications of the Fall story. Aspects of their complex portraits exploring the “esse” of women and its consequences for considering women’s relationship to knowledge become sedimented into Milton’s portrait of Eve in Paradise Lost, only to be reworked in Mary Astell’s 1694 A Serious Proposal. What in Speght and Sowernam begins as a negotiation of women’s sense of “esse” or self in portraits of the first woman becomes interrogated through Milton’s Eve to become a full-blown articulation of women’s “self-knowledge” in Astell’s argument for female education.