QuoteItemProductOption.php

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<?php
namespace Magento\Catalog\Model\Plugin;

use Magento\Quote\Model\Quote\Item\ToOrderItem as QuoteToOrderItem;
use Magento\Quote\Model\Quote\Item\AbstractItem as AbstractQuoteItem;
use Magento\Catalog\Api\Data\ProductCustomOptionInterface as ProductOption;

class QuoteItemProductOption
{
    public function beforeConvert(
        QuoteToOrderItem $subject,
        AbstractQuoteItem $quoteItem,
        $data = []
    ) {
        if (!is_array($quoteItem->getOptions())) {
            return;
        }

        foreach ($quoteItem->getOptions() as $itemOption) {
            $code = explode('_', $itemOption->getCode());

            if (!isset($code[1]) || !is_numeric($code[1])) {
                continue;
            }

            $option = $quoteItem->getProduct()->getOptionById($code[1]);

            if (!$option || $option->getType() != ProductOption::OPTION_TYPE_FILE) {
                continue;
            }

            try {
                $option->groupFactory($option->getType())
                    ->setQuoteItemOption($itemOption)
                    ->copyQuoteToOrder();
            } catch (\Exception $e) {
                continue;
            }
        }
    }
}