Child adjustment and parenting were examined in twenty-three 9–16-year-old youth from families affected by maternal HIV infection and 20 same-age peers whose mothers were not infected. Children whose mothers were seropositive reported significantly more externalizing problems. Infected mothers reported less age-appropriate supervision/monitoring relative to non-infected mothers. Better mother-child relationship quality and less impairment in parental supervision/monitoring of age-appropriate youth behaviors were associated with fewer externalizing difficulties among the HIV-positive group only. Similarly, only among HIV-infected mothers was refraining from engaging in inconsistent disciplinary tactics associated with lower reports of internalizing and externalizing problems. These data highlight the promise of programs targeting parenting skills to prevent or ameliorate child difficulties.