Despite significant advances in invertebrate phylogenomics over the past decade, the higher-level phylogeny of Pycnogonida (sea spiders) remains elusive. This group of arthropods appeared early in the fossil record, with the oldest unambiguous fossils dating to the Silurian. Due to the inaccessibility of some small-bodied lineages, few phylogenetic studies have sampled all sea spider families. In addition, previous efforts based on a handful of genes have yielded unstable tree topologies from one analytical approach to the next. Here, we inferred the relationships of 89 sea spider species using targeted capture of the mitochondrial genome, 56 conserved exons, 101 ultraconserved elements, and three nuclear ribosomal genes. We inferred molecular divergence times by integrating morphological data for fossil species to calibrate 15 nodes in the arthropod tree of life. This integration of data classes resolved the basal topology of sea spiders with high support. The enigmatic family Austrodecidae was resolved as the sister group to the remaining Pycnogonida and the small-bodied family Rhynchothoracidae as the sister group of the Page 3 of 31 robust-bodied family Pycnogonidae. This stable, dated phylogeny of Pycnogonida enables confident polarization of of cephalic appendage loss across pycnogonid families, with the consistent lack of the adult chelifore in a grade of basally diverging lineages. Molecular divergence time estimation recovered a basal divergence of crown group sea spiders in the Ordovician. Comparison of diversification dynamics with other marine invertebrate taxa that originated in the Paleozoic suggests that sea spiders and some crustacean groups exhibit resilience to mass extinction episodes, relative to mollusk and echinoderm lineages.