Building on prior work on criminal stigma, this article presents empirical findings on how criminal stigma operates within a confined environment: a transitioning house in Chicago. The study adopts an ethnographic case study approach. Empirical data consist of 116 hours of participant-observation, eight interviews and eighteen self-administered surveys. The study investigates whether or not a halfway house provides a metaphorical “safe umbrella” from criminal stigmatization for previously incarcerated individuals. This research includes attempts for and threats to the formation of this “safe umbrella”. Staff members and guest speakers provided structured opportunities (e.g. cognitive behavioral therapy, employment and self-concept coaching) for residents to discuss emotion, weakness and self- reliance as a response to actual or expected stigma from the outside world. However, threats to this “safe umbrella” occurred infrequently. This included the feeling of being labeled by speakers, staff or fellow residents, as well as reluctance in receiving assistance on stigma management. While occasional stigmatization operated within this confined and unique setting, this paper concludes that available services created a safe, welcoming and supportive “umbrella” for previously incarcerated clients.