Prior research indicated that African American and Caucasian youth respond differently to items on the Massachusetts Youth Screening Instrument–Version 2 (MAYSI-2), a mental health screening tool used nationwide in juvenile justice systems, thus possibly affecting mental health need identification. To explore the cause for the differences, cognitive interviews were conducted with eight African American and eight Caucasian male juvenile detainees, aged 12 to 16 years, from two Midwestern detention facilities. Results indicate differences in how both groups interpreted certain mental health symptoms and the dimension of time. Both groups also similarly misinterpreted and were suspicious of some items. To address these issues, the MAYSI-2 could benefit from further examination and development.