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Between 2014 and 2017, more than 40 law schools and likely well over 1000 law students engaged in learning within immigration family detention centers. The Trump Administration’s “zero tolerance” policy and implementation of wide-scale family separation in 2018 led to increased involvement by professors and students in the constantly shifting landscape of immigration detention. As the detention of immigrant families becomes increasingly entrenched, this article hits the pause button and assesses the benefits and challenges of the various approaches to, and proposes some principles for, law student engagement in this crisis lawyering in immigration detention centers, for families, and beyond.