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Asio flammeus sandwichensis
The Pueo or Hawaiian short-eared owl is Hawaii's only native owl and a ground nesting bird. This individual was spotted at dusk, at its typical hunting time. It can be distinguished from the common barn owl from the overall darker color, dark patches around its eyes and smaller/bulkier frame.
This owl was seen on Hawaii Route 200, which traverses forests, grasslands, desert and mountains. Pueos can be found from sea level to an altitude of 8000 feet. They are not found outside of Hawaii.
It is endangered on Oahu and the population on other Hawaiian islands, such as the Big Island, is not known. According to Hawaiian lore, owls are guardians that save and guide lost souls. My first owl spotting marks #600! :)
Oh my gosh, ForestDragon, I'm excited to be wrong! When I spotted this owl in person, I saw two more individuals within minutes of the first sighting and felt sure that I had seen pueos. Later, I read that the pueo was elusive (vs the common barn owl), so I based my ID on probability and silhouette. Upon closer inspection, though, my owl has dark eye patches, so you're right! :)
I think you have spotted a Pueo. The shape of the body and face don't quite match a Barn Owl (to me).