Social insects are ecologically dominant because of their specialized, cooperative castes.Reproductive queens lay eggs, while workers take part in brood rearing, nest defense, and foraging.These cooperative castes are a prime example of phenotypic plasticity, whereby a single genetic code gives rise to variation in form and function based on environmental differences.Thus, social insects are well suited for studying mechanisms which give rise to and maintain phenotypic plasticity.At the molecular level, phenotypic plasticity coincides with the differential expression of genes.This dissertation examines the molecular evolution of genes with differential expression between discrete phenotypic or environmental contexts, represented chiefly by female queen and worker castes in social insects.The studies included herein examine evolution at three important levels of biological information: (i) gene expression, (ii) modifications to DNA in the form of methylation, and (iii) protein-coding sequence.From these analyses, a common theme has emerged: genes with differential expression among castes frequently exhibit signatures of relaxed selective constraint relative to ubiquitously expressed genes.Thus, genes associated with phenotypic plasticity paradoxically exhibit modest importance to overall fitness but exceptional evolutionary potential, as illustrated by the success of the social insects.