As the Italian thirst for excellence and knowledge burgeoned throughout the Quattrocento, the genre of instructional literature responded accordingly to social demands. Offering advice on a wide range of experience from the quotidian to the extraordinary, from superstition to scientific, conduct manuals appealed to readers of all Italian social classes. Investigating the relationship between this body of literature and the lives of contemporary women, this paper will focus specifically on those manuals which prescribe behaviors for women, and will investigate the reception of these precepts and the extent in which these notions informed and transformed women's lives. In order to better understand this complex relationship, I will focus on one particular piece of advice which recurs throughout instructional literature during this time: the prescribed notion that women should remain far removed from their household windows for the sake of their honor, reputation and chastity. The adherence to such an idea would prohibit women's use of their household windows, confining them to the deep recesses of the home, far from public view and public life. Widely read manuals, such as Alberti's Della Famiglia and Barbaro's Trattati delle donne, promulgated windows as literal "windows of opportunity" to further vice, such as lust, adultery, vanity and profligacy. Furthermore, these concerns are addressed in texts beyond the realm of the prudent, instructional literature; the theme recurs as metaphor for deviancy in both popular fiction and contemporary women's portraiture. Boccaccio's Decameron, a book which conduct manual authors continually deemed inappropriate for women, features several tales in which women carry out affairs by way of their bedroom windows. Within the genre of portrait painting, both Fra Filippo Lippi and Botticelli painted interior scenes which featured women positioned at windows. The synthesis of these seemingly disparate sources, hitherto unexplored within the same context, reveals a complicated moral climate that undoubtedly had decisive consequences for Italian women during the fifteenth century.