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Abstract Satellite scatterometers provide the only regular observations of surface wind vectors over vast swaths of the world oceans, including coastal regions, which are of great scientific and societal interest but still present challenges for remote sensing. Here we demonstrate systematic scatterometer wind errors near Hawaii's Big Island: Two counter‐rotating lee vortices, which are clear in the International Comprehensive Ocean‐Atmosphere Data Set ship‐based wind climatology and in aircraft observations, are absent in the Jet Propulsion Laboratory and Remote Sensing Systems scatterometer wind climatologies. We demonstrate similar errors in the representation of transient Catalina Eddy events in the Southern California Bight. These errors likely arise from the nonuniqueness of scatterometer wind observations, that is, an “ambiguity removal” is required during processing to select from multiple wind solutions to the geophysical model function. We discuss strategies to improve the ambiguity selection near coastal mountains, where small‐scale wind reversals are common.