How can I force re-uploading of my images?

Follow these steps:

Click on the menu option

Manage > Listing Templates (For Listing Templates) OR Manage > Listings (For Listings)

Select one/mote items from the Grid.

Do right click anywhere inside the Grid. You will see a bunch of options displayed as shown below:

For Listing Templates:

For Listings:

Click on the option "Clear all Uploaded images" (for Templates) OR "Re-Upload images" for Listings. This will clear the Uploaded Path of all the pictures for all the selected items. This will force the pictures to be re-uploaded to the picture hosting site when the item is submitted to eBay.