Research Findings: There is growing evidence that home learning stimulation that includes informal numeracy experiences can promote math-related learning in school. Furthermore, national studies suggest that children who start kindergarten with stronger math skills are more likely to succeed in high school. This study used a large sample of African American boys to examine family, neighborhood, and demographic predictors of math achievement at kindergarten entry. Hierarchical regression analyses revealed that mothers who engaged in more frequent home learning stimulation that included informal numeracy experiences (e.g., playing counting games) had sons who entered kindergarten with more advanced math skills. In addition, older, more educated mothers with fewer children living in their homes had sons with more advanced math skills at kindergarten entry. Practice or Policy: Findings suggest that home-based parent involvement that helps children make sense of numbers in ways that are meaningful for them can promote math skills at kindergarten entry.