This study used in-depth observations to investigate the differences in digital literacy among African American young adult Internet users. Sampled Internet users participated in one-to-one real-time observation sessions, in which each user completed Internet-related functions in two dimensions: (1) information search and (2) privacy protection. Observations recorded whether and how quickly each participant completed the assigned tasks. We found that few participants were able to complete assigned information tasks and could control basic features in browser settings. The findings also indicated that levels of digital literacy were more related with their online access experiences than with sociodemographic characteristics. We discussed policy implications of the findings and suggested potential areas of policy concern and remedies.