Entering jail is an assault on the senses. While volunteers and inmates might share visceral experiences of entering the institution, to enter "into" jail is not the same as being "in" jail. To be "in" is to be monitored--watched and listened to without exception or reprieve. To be in jail is to follow unwritten laws of behavior and written but unvoiced rules of engagement. To be in jail is to exist under the constant gaze of captors and yet remain unseen, voices unheard, despite unrelenting surveillance. This essay explores the complicated relationship between jailed selves and self-publication through the lens of university-sponsored writing workshops, such as the SpeakOut! writing workshop. The SpeakOut! writing workshop is a program sponsored by Colorado State University's Community Literacy Center, whose mission is "to create alternative literacy opportunities in order to educate and empower underserved populations." The authors' experience with the writers at a county jail in northern Colorado suggests that there are multiple moments of engagement that offer varied opportunities to publish self/self-publish. Throughout this essay, the authors articulate the tensions that emerge between a hopeful spirit of engagement and the powerful responsibility that comes with institutional literacy sponsorship both in practice and publication.