Researchers have documented the power of legal officials to administer sanctions, from arrest to court surveillance and incarceration. How do those subject to punishment interact with officials and attempt to subvert their power? Drawing on interviews and ethnographic observations among 63 criminal defendants and 42 legal officials in the Boston-area court system, this article considers how socioeconomically and racially disadvantaged defendants interact with their defense attorneys, and with what consequences. Given racialized and classed constraints, many disadvantaged defendants mistrust their court-appointed lawyers. Their mistrust often results in withdrawal from their lawyers and active efforts to cultivate their own legal knowledge and skills. Defendants use their lay legal expertise to work around and resist the authority of their lawyers. Defense attorneys and judges respond with silencing and coercion, given the unwritten norms and rules of the court. These findings complicate existing accounts of disadvantaged defendants as passive actors and contribute to cultural sociological and relational theories of how people engage with professionals across institutional spaces. Unlike in mainstream institutions such as schools and hospitals where self-advocacy is rewarded in interactions, criminal court officials reject disadvantaged defendants’ attempts to advocate for themselves.