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Women with felony convictions encounter significant barriers during reentry, particularly in securing employment and housing. These barriers are shaped by stigma, background check policies, and limited access to supportive resources, often leading to instability and feelings of isolation. This study analyzes Reddit posts made by self-identified women in the r/Felons subreddit to understand how they describe these barriers and how they use online spaces for support. A qualitative content analysis was used to identify common themes related to employment, housing, and stigma. Many posts reflect frustration, discouragement, and anger toward the criminal justice system and reentry process. Women frequently described limited employment options and expressed reluctance to pursue jobs they perceived as traditionally masculine. They emphasized a desire for stable and dignified work. Women also sought advice, shared personal experiences, and wanted to engage with others who shared similar backgrounds. This research highlights how online communities can serve as both emotional outlets and informal support systems. Understanding these spaces provides insight into women’s reentry experiences and emphasized the importance of considering gendered barriers in reentry research and policy.