For many people, sharing content across a range of social media services is a familiar and integral part of life. Yet, the same cannot be said about the 1.5 million incarcerated men and women in U.S. prisons who have limited to no access to the web. Even with strict restriction and regulation, many prisoners have found ways to connect online with friends, relatives, and strangers through contraband cell phones, friends and family who manage their profiles, or third parties that link them to social networks. Moreover, organizations, such as Write a Prisoner, Black and Pink, and Meet an Inmate give prisoners the opportunity to list a profile online in hopes of acquiring a pen-pal, a new friend, and a connection to the outside world. For a population often misrepresented and stigmatized, websites like these open up new ways of reconstructing their identity, finding support, and building social capital. Despite the potential benefits of prison pen-palling, there is a paucity of research about prison correspondence and support from individuals not known to the inmate prior to incarceration. This study seeks to fill this gap by exploring prison pen-pal soliciting profiles, what common themes exist within these personal ads, what are inmates’ motivation for joining Write a Prisoner, what levels of support are inmates seeking in pen-pals, how are inmates expressing desistance and changes in identity on their profiles, and how do inmates perform masculinity on their personal ads. Findings indicate inmates are seeking various types of support including friendship, romance, non-judgmental support, and reentry support. The findings in this study support research on desistance and redemption narratives. Additionally, they bring attention to how inmates present themselves through hegemonic masculinity. The results of this study can help guide appropriate policy regarding inmate personal ads as states move to ban the practice, and lead to the development of befriending and pen-palling programs in the United States.