Listings won't Upgrade

I am still in test mode of my site. I am trying to create a way for users to claim listings I have previously made and have the option to upgrade from free to paid listings with different features.

So far, I have created a free listing and a $5 listing with front page enhancement. When I go into a free listing and go to “Edit Listing” I have the option to upgrade from free to $5 enhanced listing.

Currently, everything works as far as upgrading and payment for the listing. However, the enhancements do not turn on and the listing does not show up on the homepage. I have a “recent listings” section setup to only show front page enhanced listings.

In the listing manager, front page enhanced does not change from “no” to “yes”. If one creates a listing from scratch choosing the $5 enhanced listing, then everything works fine.

Any Ideas as to why upgrading does not work? How can I fix this?