New genomic resources allow for the investigation of gene family diversity in genome-enabled reptiles. The Toll-like Receptor (TLR) gene family recognizes pathogen-associated molecular patterns (PAMPs) and coevolves with environmental pathogens which makes it a strong candidate for looking at the interplay between gene family diversification and host-pathogen coevolution. Using a new orthology curation pipeline and phylogenetic reconstruction, a novel gene expansion event of TLR8 was identified to be exclusive to crocodilians and chelonians with species-specific pseudogenization events. A new gene, TLR21-like, was identified as a part of the TLR11 subfamily. These findings uncover reptile-specific gene family evolution and provide indications of the role of habitat in this process.