The current study attempted to investigate the nature and impact of home math talk of low-income primary caregivers of Head Start children during home cooking (N = 46). Using hierarchical regression analysis, we examined the predictability of total math talk and specific types of math talk (i.e., number talk, operation talk, and measurement talk) for children's math skills assessed in the fall and spring of their preschool year. Caregivers' total math talk was not concurrently associated with children's fall math skills, but number talk was associated with fall math. For spring math skills, there were no main effects of any type of math talk, but interaction effects were identified. Specifically, total math talk and measurement talk did not contribute to spring math skills in children when the math talk was not accompanied by high-level task-orienting talk that explained and organized cooking task processes. Caregiver number talk could help initial math skills of children who are environmentally at risk. Continued math skills development may be stimulated by measurement talk, especially when caregivers frequently provide measurement talk along with task-orienting scaffolding.