The COVID-19 pandemic has laid bare entrenched health inequalities in the U.S. health care system faced by structurally marginalized immigrant communities. Deferred Action for Childhood Arrivals (DACA) recipients are well suited to address these social and political determinants of health due to their large presence in service positions and skill sets. Yet their potential in health-related careers is limited by unique barriers related to uncertainty about their status and training and licensure processes. We report findings from a mixed-method (interview and questionnaire) study of 30 DACA recipients in Maryland. Nearly half of participants (14; 47%) worked in health care and social service fields. The longitudinal design featured three research phases conducted between 2016 and 2021, which enabled us to observe participants’ evolving career trajectories and capture their experiences during a tumultuous period (due to the DACA rescission and COVID-19 pandemic). Using a community cultural wealth (CCW) framework, we present three case studies that demonstrate challenges recipients encountered as they embarked on health-related careers, including protracted educational journeys, concerns about program completion/licensure, and uncertainty about future employment. Yet participants’ experiences also revealed valuable forms of CCW they deploy, including building on social networks/collective knowledge, forging navigational capital and sharing experiential knowledge, and leveraging identity to devise innovative strategies. Results highlight the critical value of DACA recipients’ CCW that renders them particularly apt brokers and advocates in promoting health equity. Yet they also reveal the urgent need for comprehensive immigration and state-licensure reform to promote DACA recipients’ inclusion in the health care workforce.