Technical probation violations are common among probation-involved youth and, across many jurisdictions, may result in detention or residential placement. The current study examined prevalence of technical violations occurring during one's first probation period, the average time to technical violation, and individual-level and justice-related factors related to technical violations among probation-involved youth in a juvenile justice system. We analyzed electronic criminal records of 18,289 probation-involved youth following their first arrest (68.7% male, 53.9% Black, Mage ϭ 15.2 years). Technical violation was defined as a violation resulting from a noncriminal incident. We examined effects of charge severity, probation conditions (e.g., electronic monitoring), and program referrals (e.g., mental health) on likelihood of technical violation utilizing survival analysis stratified by race. Across 18,289 youth, 15.3% received a technical violation during their first probation; Black youth violated more quickly compared with White youth (log-rank test p Ͻ .001). In multivariate survival analyses, the hazard for time to technical violation was higher for Black youth compared with White youth (p Ͻ .001), males (p ϭ .04), and younger youth (p Ͻ .001). Youth assigned to more probation requirements violated more quickly. Electronic monitoring and education, mental health, and drug programs were associated with shorter time to violation, controlling for race, ethnicity, and charge severity. Black youth violate more quickly compared with White youth. Across all youth, assignment to more probation requirements increased risk of technical violation and shorter time to violation. Despite the benefit of probation interventions, system-level efforts are needed to help youth adhere to probation requirements and successfully complete probation.