The behavior @cihadturhn explains seem to be what I'm able to replicate: If you are on iOS 14.5 and disable apps tracking you: you have to enable it, then (sometimes) sign out/back into iCloud.
If you are on iOS 14.5 and disable apps tracking you, then update to iOS 14.5 with it disabled: You have to factory reset and NOT restore from an iCloud backup. Disabling it and signing out/back into iCloud does not cause the permission request to go through.
cddict
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