Song Authorization in iTunes

Greetings all. I recently imported my iTunes library from a previous PC to my newly purchased Macbook

Pro running Catalina. I authorized my Mac to play songs via the Authorizations tab under Account. As I browse the newly imported library and click songs that were purchased in iTunes in the past, iTunes tells me the song is unauthorized to play on the computer and prompts me to authorize it by entering my apple user ID and password. I do so. It then tells me the song is now authorized to play. When I click on the song again, get the same message telling me the song is unauthorized to play. There are other purchased songs from the iTunes Store that do play without authorization. Can someone shed some light on what is going on. Obviously I want access to all of my purchases from the iTunes Store and since I have authorized this computer to play, I don't see why I am having an issue. At this point I have only used 2 out of 5 possible authorizations. All help would be appreciated.