In this article a group of seven Latina/o immigrants, parents, advocates, and ethnographers draw on critical race theory to explore what it means to co-present on, and engage in, difficult conversations about immigration and documentation status. We theorize how, through critical collaboration motivated by our joint presentation, we co-constructed counterspaces in which, while interrogating what we tend to count as knowledge and expertise in education research, we could address not only the difficulty of communicating with teachers about issues surrounding documentation status, but also of knowing how to approach this topic with children and with each other. We argue that these carefully crafted counterspaces created opportunities to push beyond our traditional norms, breach silences, and open up ways in which to reposition the safety of engaging in conversations regarding undocumented status with our children, communities, educators, and with each other.