Do expert witnesses enable legal violence by participating in a repressive immigration system? Drawing from over 20 years of court watching, accompaniment, and expert witness testimony, this article discusses some of the complications, contradictions, and ethical dilemmas in applying anthropological knowledge to immigration proceedings particularly for child applicants. For example, how might we effectively support individual claims to limited forms of legal relief while not essentializing cultures and countries? How do we resist reductive claims that victimize children and pathologize their parents? This is profoundly challenging, yet also a powerful opportunity. As in fieldwork, engaging with these dilemmas in practice often yields productive insights into how we might educate attorneys and judges from within.