Are you displaying the wrong image for your products inside ShippyPro?
The reason can be really simple.
In case you have different products, you'd need that each product has a different SKU: otherwise in case of repeated SKUs and different image, only the first image will be displayed for each one.
To sum up, just remind to follow this super understandable rule:
1 SKU = 1 Image
How can I add a new image for my item? 💡
In order to update the image you will need to associate a new SKU for the item with the updated image.