I have gone over the documentation for User Upgrades and have no issue in setting up and getting the purchases to go through; however, it seems that neither manually nor automatically, are the secondary groups being applied after the purchase or manually added. The user remains in the Registered user group and no secondary group is added.
The users are listed under Active User Upgrades, as well, their accounts are associated with the upgrade.
Screenshots of settings:
I have run the cron jobs to ensure upgrades and expired upgrades have been done, as well, I have used all the tool options to rebuild everything. I have had the user log in and out to ensure that it isn't user dependent. There are no permissions that have NEVER set. Additionally, I have checked the Transaction Log and there are no errors.
I'm at a complete loss as to how this system is suppose to function, if not to have the user assigned to the temporary group for as long as the upgrade is available to them.