Uploading two image files for two products...possible?

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I have a custom product page with a product form. The form includes an image upload. There are no apps being used on this product page.

The user has the option to 'Add another product' once they complete the initial form and this will duplicate the the product form to allow them add another product + image upload.

However when they then proceed to the cart, only the last image will be brought into the cart and the original image will be lost. Is it possible to have both images come into the cart, can someone please explain the logic behind this?

Many thanks!