We live in a country with a long history of settler colonialism and we understand that our educational institutions, structures, and ideologies are part of that history. Our perceptions as educators of how students learn and how we should lead can be grounded in implicit biases that may dehumanize learners and perpetuate systems of oppression. Using the "testimonio" of two site principals in New York and California within a broader practitioner research framework we explore the manifestations of captivity, carcerality, and COVID-19 in our lived realities. As educators we are in part complicit in the tracking and creating a vantage point where our students are being seen. We experience tensions. We are committed to our educational "responsibilities to love and serve our students and community" and not allow ourselves the privilege of ignoring, of acting like the racializing of our community does not affect us.