This essay describes and takes up the task of what the authors call threading the needle—teaching difficult content with a critical lens while simultaneously teaching with a trauma-informed pedagogy. Drawing data from three qualitative studies, one focused on teachers teaching for social justice in unjust school spaces, another looking at how teachers teach war to the children of soldiers, and a third how teachers teach lynching in schools near historic lynching sites, this manuscript argues that threading the needle is made more difficult by a too generalized definition of trauma informed teaching, shortsighted professional development on the topic, and too little direction on pedagogy. This leaves teachers feeling adrift and subtly signaled to avoid teaching difficult content with a critical lens, confirming for some teachers the absence of teaching controversial topics of race, class, gender, sex, and resistance altogether while others teach critically, but quietly, outside the watchful eye of the school