The evolution of live birth from the parent’s reproductive tract involved a profound shift in animal life histories; independent developmental stages were eliminated from the life cycle. Although rare, marine invertebrate clades that contain species with live birth often have several viviparous lineages. The family Asterinidae, a species-rich sea star taxon prone to life history evolution, exemplifies this. Viviparity has evolved independently four times in asterinids through strikingly different evolutionary pathways; by punctuate evolution on the fringe of ‘parental’ species distributions. This has created a suite of cryptic morphospecies distributed from northern Australia and through Indonesia to Japan. We use molecular phylogeny to discern previously undetected species diversity and phylogenetic hypotheses to reconstruct the direction and number of evolutionary transitions involved with the evolution of live birth in these sea stars. This has lead to discovery of several new species from the Great Barrier Reef.