Terrestriality, the adaptation to life on land, is one of the key evolutionary transitions, occurring numerous times across the tree of life. Within Arthropoda, there have been several independent transitions: in hexapods, myriapods, arachnids and isopods. Isopoda is a morphologically diverse order within Crustacea, with species adapted to almost every environment on Earth. The order is divided into 11 suborders with the most speciose, Oniscidea, including terrestrial isopods such as woodlice and sea-slaters. Recent molecular phylogenetic studies have challenged traditional isopod morphological taxonomy, suggesting that several well-accepted suborders, including Oniscidea, may be non-monophyletic. This implies that terrestriality may have evolved multiple times. Current molecular hypotheses, however, are based on limited sequence data. Here, I collate available genome and transcriptome datasets for 36 isopods and four peracarid crustaceans from public sources, generate assemblies and use 970 single-copy orthologues to estimate isopod relationships and divergence times with molecular dating. The resulting phylogenetic analyses support monophyly of terrestrial isopods and suggest conflicting relationships based on nuclear ribosomal RNA sequences may be caused by long-branch attraction. Dating analyses suggest a Permo-Carboniferous origin of isopod terrestriality, much more recently than other terrestrial arthropods.