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As of macOS Big Sur 11.1, there's a setting in "System Preferences" » "Apple ID" » "Media & Purchases". Change "Free Downloads" from "Require Password" to "Never Require".


I’ve had this problem repeatedly (including today) with the Mojave installer where it leaves behind the DMG file (5GB+) in the trash an nothing will delete it. The only way I have found to delete it is to boot to recovery mount the boot (data) partition open Terminal manually CD into the .Trash folder (or Users/user/.Trashes) then rm -rf "Install macOS ...

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