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In response to COVID-19, the CDC issued hygiene, protective equipment, and physical distancing guidelines to reduce virus transmission. Adherence was crucial for public health, particularly in the earliest stage of COVID-19, before effective treatments emerged. Still, there was wide variation in willingness and/or ability to follow the recommendations. One group that might be expected to flout rules and take risks under normal circumstances is adolescents. This developmental stage predisposes one to push boundaries and seek the company of peers. Adolescents with a history of lawbreaking might be even more inclined to disregard public health guidelines due to experiential and dispositional factors. We employed a longitudinal study launched prior to the pandemic to identify which pre-pandemic factors predict adolescents’ adherence to—or disregard for—public health guidelines during a crisis. The sample (N = 75, 30% justice-involved) came from predominantly minoritized communities in a southwestern U.S. city. Data were collected in three waves over one year. Analyses tested whether adherence varied by time period, local infection trajectories, justice involvement, pre-pandemic mental health, risk-taking, and rule orientation. Results revealed that adherence declined over time and was generally lower among justice-involved adolescents. In addition, justice-involved adolescents with higher depressive symptoms displayed lower adherence, whereas those reporting higher anxiety symptoms displayed higher adherence. Understanding these factors is crucial for developing strategies to promote adherence to public health guidelines among adolescents during public health emergencies.