WASHINGTON (AP) — In a patent fight with Apple, Samsung is asking the Supreme Court to take a digital-age look at a type of dispute it last confronted in the horse-and-buggy era.

South Korea-based Samsung on Monday appealed a $399 million judgment for illegally copying patented aspects of the look of Apple’s iPhone, the latest round in a long-running fight between the two tech industry giants.

The last time the Supreme Court heard cases on patents covering the appearance of a product — instead of the way it works — was in the late 1800s. That’s when court battles concerned designs of spoon handles, carpets and saddles.