Adolescents and young adults (AYA) have poorer retention, viral suppression, and survival than other age groups. We evaluated correlates of initial AYA engagement in HIV care at facilities participating in a randomized trial in Kenya. Retrospective cohort study. Electronic medical records from AYA ages 10-24 attending 24 HIV care facilities in Kenya were abstracted. Facility surveys assessed provider trainings and services. HIV provider surveys assessed AYA training and work experience. Engagement in care was defined as return for first follow-up visit within 3 months among newly enrolled or recently re-engaged (returning after >3 months out of care) AYA. Multilevel regression estimated risk ratios and 95% confidence intervals (CIs), accounting for clustering by facility. Final models adjusted for AYA individual age and median AYA age and number enrolled per facility. Among 3662 AYA records at first eligible visit, most were female (75.1%), older (20-24 years: 54.5%), and on antiretroviral therapy (79.5%). Overall, 2639 AYA returned for care (72.1%) after enrollment or re-engagement visit. Engagement in care among AYA was significantly higher at facilities offering provider training in adolescent-friendly care (85.5 vs. 67.7%; adjusted risk ratio (aRR) 1.11, 95% CI: 1.01-1.22) and that used the Kenyan government's AYA care checklist (88.9 vs. 69.2%; aRR 1.14, 95% CI: 1.06-1.23). Engagement was also significantly higher at facilities where providers reported being trained in AYA HIV care (aRR 1.56, 95% CI: 1.13-2.16). Adolescent-specific health provider training and tools may improve quality of care and subsequent AYA engagement. Health provider interventions are needed to achieve the '95-95-95' targets for AYA.