Copyright: © 2020 Olszewski et al. This is an open access article distributed under the terms of the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original author and source are credited. Cuscuta (dodders) is a group of parasitic plants with tremendous economic and ecological significance. Their seeds are often described as “simple” or “unspecialized” because they do not exhibit any classical dispersal syndrome traits. Previous studies of seed morphology and/or anatomy were conducted on relatively few species. We expanded research to 101 species; reconstructed ancestral character states; investigated correlations among seed characters and explored allometric relationships with breeding systems, the size of geographical distribution of species in North America, as well as the survival of seedlings. Seed morphological and anatomical characters permit the separation of subgenera, but not of sections. Identification of Cuscuta species using seed characteristics is difficult but not impossible if their geographical origin is known. Seeds of subg. Monogynella species, exhibit the likely ancestral epidermis type consisting of elongated and interlocked cells, which are morphologically invariant, uninfluenced by dryness/wetness. Subgenera Cuscuta, Pachystigma and Grammica have evolved a seed epidermis with isodiametric cells that can alternate their morphology between two states: pitted when seeds are dry, and papillose after seed imbibition. A seed coat with double palisade architecture throughout the entire seed has also apparently evolved in subgenera Cuscuta, Pachystigma and Grammica, but several species in two clades of the latter subgenus reverted to a single palisade layer outside the hilum area. The same latter species also evolved a peculiar, globose embryo, likely having a storage role, in contrast to the ancestral filiform and coiled embryo present throughout the remainder of the genus. Autogamous species had on average the highest number of seeds per capsule, whereas fully xenogamous taxa had the lowest. No correlation was revealed between the size of the seeds and the size of their geographical distribution in North America, but seedlings of species with larger seeds survived significantly longer than seedlings resulted from smaller seeds. Diversity and evolution of seed traits was discussed in relationship with their putative roles in dormancy, germination and dispersal.