Hi, I was able to finish my testing today. On a clean install of DNN 5.2.3 with store 2.1.31both PayPal IPN and the triggers work without error. On an upgraded DNN site with SSL and other settings configured for security IPN still fails. What is the error you are getting on the triggers?

Yes. Since you did not get an error and the status was updated to Paid but the role was not added I think the issue is with the configuration of the ProductRoles table. Check the RoleID from the Roles table in DNN that you want to unlock along with the ProductID from the Store_Products table and make sure they have been added correctly to the v05_Store_ProductRoles Table. You will need to update the table as you add or delete products or roles or if the keys change when you reinstall the Store module or migrate to a new portal. Also, the portal is hard coded to 0 which is the root portal but if you run sub portals that will not work. Whether you use PayPal IPN or the drop down list in the store to change the Status to Paid the trigger should still function because it operates at the table level. This should generate an error on the page if anything is wrong with the triggers themselves. If the triggers fail the database should not update the status from Awaiting Payment to Paid either.