Hi PhilthyCollins,
Thanks for contributing to our forum. Our Upload from File tool currently only supports the addition of one image per listing so, in order to add multiple images to a listing you are uploading from a CSV file, you would need to add each image after the first by editing the item from your Saved Listings page once it has been uploaded.
I have shared your comments in this regard with our Product Management team though and we will take them into consideration when planning future updates to our site.
We appreciate the feedback. If you need any further assistance with your account, please feel free to contact our Customer Support team by mousing over the “Help” tab on our site and selecting the “File Support Case” option.
-Mike