Custodial grandmothers and grandchild (aged 4 to 12) dyads (N = 170) completed self-report, other-report, and an observational task that captured child HI, expressive social support, and custodial grandmother-grandchild compliance variables. A multivariate analysis of covariance tested differences between high and low hyperactivity-inattention on observed parenting variables while controlling for child age. While overall results were not significant, there were significant differences between child age and observed parenting variables. A hierarchical regression model revealed that, when controlling for age, child hyperactivity-inattention does not moderate the relationship between commands given by a custodial grandmother and child compliance, but revealed that direct commands from the grandmother predicted compliance. A second hierarchical regression model suggested that encouragement and praise (versus criticism and discouragement) from a grandmother moderated the relationship between grandmother commands and child compliance, when controlling for child age. It appeared that when grandmothers gave indirect commands more frequently, encouragement and praise instead of criticism was associated with greater compliance. In dyads with frequent direct commands given, compliance was high, however dyads who scored high in direct commands with criticism and discouragement were most likely to comply. This study adds to the literature by providing insight into the challenges and strengths for …