Birds are among the most mobile organisms on the planet: many species routinely perform long-distance migrations that require remarkable feats of physical endurance and complex navigation. Rarely, individual long-distance migrants may make movements in exceptional directions, placing them beyond their species’ ordinary distributions and providing the potential for significant ecological developments, such as the colonization of a new region by the vagrant species, the introduction of novel parasites or pathogens, or the dispersal of seeds and fungal spores. We detail the occurrence of a Dark-sided Flycatcher (Muscicapa sibirica), a highly migratory passerine species typically found in east Asia, at an urban site in California on 17–19 September 2025, establishing the first record of this species and genus for temperate North America. We age this individual as a first-fall bird and discuss molt strategies in the genus Muscicapa. We identify it as a member of the nominate subspecies, therefore likely originating from highly migratory populations that breed in northeast Asia. We evaluate mechanisms by which this individual may have arrived in California and discuss the concepts of reversal misorientation and mirror-image misorientation, modes of anomalous navigation that may provide explanations for Palearctic-Nearctic vagrancy in highly migratory Asian passerines. Our observation represents a noteworthy addition to the known avifauna of temperate North America. In documenting this occurrence, we draw attention to the remarkable but little-studied process of long-distance vagrancy in migratory birds.