This essay attempts to disable the “ruinous” logic that has fueled recent slut-shaming on Web 2.0 by making visible the ways in which our machines are promiscuous—routinely “leaking.” The authors present the leak as a habit so as to disrupt the illusion of privacy and sealed subjectivity that enables the possibility of being a “victim” of slut-shaming, revenge porn, and similar dangers of Web 2.0. They argue that blaming the user for leaks only detracts from the systematic vulnerabilities of Web 2.0. The essay looks at the pernicious practice of “ruining” young, white, female subjects through the circulation of naked or sexual images of them. This habit not only exemplifies the linking of subjectivity, privacy, and whiteness but also the way in which the online subject is figured as open, vulnerable, and perhaps asking for it—that is, traditionally female. The essay argues that rather than call for bubbles of privacy that seal off online subjects, as if to prevent their leaking or sluttiness, the inherent promiscuity of new media must be embraced.