The evolution of divergent life history strategies can be implicated in the promotion of ecological opportunity and species diversification. The Pleuroceridae (Cerithioidea) is a biodiverse and geographically widespread family of freshwater gastropods that occupy numerous freshwater ecosystems in North America east of the Rocky Mountains. Previous studies have shown substantial variability of life history traits between species. This variation is relatively unique as most freshwater gastropod families display similar life histories. In particular, egg-laying behaviors among pleurocerid species can be sorted into several unique modalities: singly-laid eggs, multiple singly-laid eggs, small individual lines of eggs, circular egg clutches, and eggs laid together in large strip-clutch formations. Here, we examine these behaviors in a robust phylogenetic context using ancestral character reconstruction to understand the evolution of these egg-laying behaviors and whether convergence shapes contemporary patterns. Our results indicate that a discrete clutch egg-laying behavior has evolved convergently at least three times with no reversals, possibly suggesting repeated evolution of increased parental investment when laying eggs. The strip clutch behavior has evolved a single time, also with no reversal. In contrast, although there are several instances of independent evolution of laying eggs singly or in single lines, these behaviors appear to be more vagile.