While there are many studies which examine the symbiotic relationship between schools and prisons, there are very few studies which center the voices and unique perspectives of Black women educators who teach, collaborate with, and learn alongside incarcerated youth and adults. Therefore, this article focuses on our storied lives as three Black women educators in carceral spaces. Utilizing kitchen table talk methodology and the analytical lens of Black Gaze Theory, this article seeks to explore the question: What internal and external factors have made it possible to pursue our work within carceral environments? As such, within this article we share and analyze our personal experiences, our ever-closeness to carcerality, and what continues to draw us to this work --interrogating ourselves alongside each other. That said, this article is also an invitation for educators, administrators, families, and community members to imagine and create liberatory educational experiences alongside, with, and for youth, adults, and community members who have experienced incarceration.