Double check theme editor settings for anything like show cart properties, or show additional cart info etc etc.
For app related customizations you need to first check with that apps support or their support docs to see if they support the desired feature or have guides, etc.
Beyond that is an advanced customization that depends on where the image exists when it's upload and the theme.
Test whether the app is uploading the image to itself or letting it be part of the cart.
Install a fresh copy of dawn and test if the images show up.
Most themes support line item properties which are meant for this type of info.
If this image is uploaded as part of a product being added to the cart...
..And if the app is uses line item properties to attach the file to the line-item(a product in a cart) like it should then in a theme like Dawn either the image or a link to the image should show up.
If you need this customization dug into then contact me directly by mail for services. Please always provide context, examples: store url, theme name, post url(s) , or any further detail. Contact Info in signature.