Why don't music purchases I make from my iPhone automatically show up in iTunes on my Mac anymore?

Even though my Mac and my iPhone both use the same AppleID, music purchases from my iPhone no longer show up in iTunes anymore! When I click on "Check for available downloads" it says "All purchases have been downloaded for this AppleID". What gives?

That setting will only apply to new purchases. To redownload your past music purchases click on your name towards the top right of the iTunes screen and then click Purchased on the popup
You should (if they are still in the store) be able to redownload them from the screen that then shows.
Or on the Store tab in Preferences tick the 'show iTunes in the cloud purchases' tickbox and any music that isn't currently downloaded should show in the Music part of your library with a cloud icon against it for redownloading - click the cloud icon to download it.
Or connect your phone and do File > Devices > Transfer Purchases to copy them over from it.

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