Premodern pregnancy was inherently precarious and uncertain. Even whether a woman was pregnant was, to some degree, unknowable. A pregnancy's terminus was its surest verification, yet health risks and diagnostic uncertainties inherent in premodern medicine meant that any pregnancy's outcome was always at issue. At the same time, the patriarchal logic of early English society necessitated some degree of certainty about pregnancy, or at least performances of such certainty. This experience of time, in which a pregnancy could not really be confirmed until it ended, and its outcome in turn provided the only certain evidence of the pregnancy's realness, is infused with epistemological uncertainty and temporal complexity. At the crux of the interpretive challenges posed by pregnancy was the maternal subject, who was at once in a position of explanatory authority, privy to the embodied experience of pregnancy, and objectified by that state, rendered as a text that others could decipher. While literary scholarship has tended to focus on unequivocally pregnant characters and definitively maternal bodies, this chapter explores some of the possibly maternal literary characters that appear in premodern texts by Geoffrey Chaucer (d. 1400), William Shakespeare (1564–1616), and John Webster (c. 1580–c. 1626–34). In these works we find women whose ambiguous maternal statuses present interpretive dilemmas for narrators and characters within texts and for their readers and audiences. These potentially pregnant characters embody epistemological uncertainties animated by female agency and the temporality of pregnancy. Across genre and time period, English writers ask how interpretable the female body is as a potentially meaningful, or morally pregnant, text.