Hi itsjustme,
Thanks for posting your question here. If you click the "Edit and Relist" link next to an item on your Closed Listings page, change the images that are selected in the Auctiva Image Selection section and then relist the item, the new images that you added to the listing should definitely appear in the resulting relist once it is active on eBay.
However, if you then clicked the “Edit and Relist” link next to the same closed listing again, it is expected that you will still see the old images you replaced because the data available on that page is not overwritten during the relist process.
I'm not sure I fully understand the work flow you used which led to this observation, but I figured I would take a crack at it. If I misunderstood the issue you described and/or if there is a specific example you would like to take a look at, please file a support case from the “Help” tab within your account.
-Mike