It’s pretty typical for a category level page to have a header image. Magento, in fact, has an area reserved for category header images. Sometimes, these images don’t upload into magento. This is usually an issue with permissions.
In order to import category images for Magneto to use, the folder that holds them must have write permissions. Once you set the permissions, you will see your category header images appearing. The folder is media/catalog/category. The product image folder can have the same issues, too. That folder is media/catalog/product.
ie: via ssh, navigate to the media file and then run the following unix command:
chmod 777 category
chmod 777 product
This will make your category and product files readable, writable, and executable for everyone. You can double check permissions using the following command:
getfacl category or getfacl product, which will print out what the permissions are for those folders. Alternatively you can use ftp to set permissions.
Your images should now be uploadable and visible in the front end.