With her combination of experience as a legal educator and scholar, attorney and social worker, Professor Caldwell brings a unique interdisciplinary perspective to the teaching of criminal law, criminal procedure, and the intersections between criminal and immigration law. She launched Southwestern’s Youth Offender Parole Clinic in 2014, which trains students to provide pro bono representation to juvenile offenders serving lengthy sentences in adult prisons.

Professor Caldwell's scholarly research focuses on immigration, criminal law, and juvenile justice. Her 2019 book Deported Americans: Life After Deportation to Mexico received many accolades and was selected as a finalist for the 2021 PEN/Galbraith Literary Award for Nonfiction. Professor Caldwell’s most recent law review was published in the UC Irvine Law Review; it argues that adolescent development principles should be incorporated into the legal analysis of key standards in California’s recently revised felony murder law.