Prior studies suggest that one anticipated benefit of bariatric surgery is the achievement of a thinner body, one that is less subject to perceived negative judgment and condemnation by others. However, additional analyses also indicate that stigma may persist even with significant post-surgery weight loss. To investigate the stigma-related perceptions and experiences of women who have undergone bariatric surgery and the resulting body transformations, we conducted individual, semi-structured interviews with thirty Brazilian women (15 aged 33–59 and 15 aged 63–72). The resulting text was then analyzed using thematic analysis. We found that some form of weight stigma persisted for our participants, regardless of weight loss. Ongoing experiences of stigma were also evidenced by the constant internal and external vigilance reported by the women, as well as their articulated efforts to distance themselves from their previous bodies. Additionally, participants reported being judged for choosing an “easy way out” to lose weight. Those in the older group reported that weight stigma was entangled with ageism: older participants received mixed messages underscoring the ways that weight and age may interact in doubly stigmatizing ways. Family and close peers were especially powerful sources of stigma experiences. Collectively, these results show that weight stigma persists even when people undergo a procedure to lose substantive weight and that the degree and types of stigma experiences are influenced by gender and age. Our study suggest future research should explore whether a targeted approach might be more effective, for example, an approach that would emphasize the importance of developing coping strategies with respect to experiences of stigma and discrimination after surgery.