Prospective studies have shown modest associations in externalizing and internalizing behaviors across generations, but none have examined associations with the growth of these behaviors in the offspring. Three generations of participants were assessed over approximately 27 years, and prediction models of growth in the third generation’s (G3) externalizing and internalizing problems across ages 3 to 9 years were examined. The sample included 103 fathers and mothers (G2), at least one parent (G1) for all of the G2 fathers (99 mothers and 72 fathers), and 185 G3 offspring (83 boys, 102 girls) of G2, with prospective data available on the G2 fathers beginning at age 9 years. Intergenerational associations in psychopathology were modest, and much of the transmission occurred via contextual risk within the family of procreation.