In this article, we contrast evolutionary and psychobiological models of individual development to address the idea that individual development occurring in prototypically risky and unsupportive environments can be understood as adaptation. We question traditional evolutionary explanations of individual development, calling on the principle of probabilistic epigenesis to suggest that individual development resulting from the combined activity of genes and environments is best understood to precede rather than follow from evolutionary change. Specifically, we focus on the ways in which experience shapes the development of stress response physiology, with implications for individual development and intergenerational transmission of reactive, as opposed to reflective, phenotypes. In doing so, we describe results from several analyses conducted with a longitudinal data set of 1,292 children and their primary caregivers followed from birth. Our results indicate that the effects of poverty on stress response physiology and on the development of the self-regulation of behavior represent instances of the experiential canalization of development with implications for understanding the genesis and “adaptiveness” of risk behavior.