Cannot delete items from Downloads folder

I was doing some maintenance on my iMac and noticed that in one account there were a large number of downloads. I logged into that account and tried to delete the files but they would not delete. I have Parental Controls enabled (only time limits) but not sure if that's the problem.

Parental controls should not be a problem. Have you tinkered with permissions on the Download folder on that account? prehaps by using "apply to enclosed items" button? That could have resulted in symptoms you are seeing. Run the following terminal command from the affected account and see if it makes a difference. Copy and paste, do not retype please.
chmod -RN ~/Downloads/*

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Cannot delete items from Downloads folder

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