This article examines whether children living with single mothers benefit when they also live with a grandparent, using data from the 1979 to 2002 waves of the National Longitudinal Survey of Youth merged mother-child file (N = 6,501). Results indicate that for White children, living with a single mother and a grandparent is associated with increased cognitive stimulation and higher reading recognition scores, compared to living with a single mother alone. For Black children, grandparent coresidence is associated with less cognitive stimulation. Thus, in some instances, living with a grandparent can benefit children, but the pattern of results differs by race.