Orb-weaving spiders are good objects for evolutionary research, but phylogenetic relationships among and within orb-weaving lineages are poorly understood. Here we present the first species-level molecular phylogeny that includes the enigmatic orb weavers 'Zygiellidae' and Caerostris. Zygiellidae is interesting for the evolution of the sector web, and Caerostris is noteworthy for web gigantism and extraordinary silk biomechanics. We assembled a molecular data set using mitochondrial (COI, 16S) and nuclear (H3, 18S, 28S, ITS2) gene fragments for 112 orbicularian exemplars, focusing on taxa with diverse web architecture and size. We show that 'Zygiellidae' contains the Holarctic Zygiella genus group (Leviellus, Parazygiella, Stroemiellus, and Zygiella) and the Australasian Phonognatha and Deliochus. As this clade is placed with Araneidae in all analyses we treat it as a subfamily, Zygiellinae. Using the new phylogeny, we show that the sector web evolved eight times, and coevolved with the silk tube retreat, but that these features are not zygielline synapomorphies. Zygiellinae, Caerostris, and some other araneids form a basal grade of araneids that differ from 'classical' araneids in web-building and preying behaviour. We also confirm that Caerostris represents the most striking case of spider-web gigantism.