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Hey, I am not so familiar with the package, but when using the orientation chained method, I cannot pass a degree other than 0, 90, 180 and 270 since the argument is type hinted to the enum Spatie\Image\Enums\Oritentation, so I thought adding a new case RotationMinus90 would be a good idea.
Image::load($media->getPath())->orientation($request->get('direction') === 'left' ? -90 : Orientation::Rotate90)->base64();