(Sorry if this is the wrong thread to be posting in, but I thought this might be useful.) I made a quick AppleScript for clearing the Downloads folder and then emptying the Trash. I put it into a script here. Here are the steps to have it run every login: Make sure to change "YOUR USERNAME" in the script to your actual username as it appears on you home folder. Go to File > Export and save the script as an application. Delete the original script. Put the application anywhere but the Downloads folder. Go to > System Preferences > Users & Groups > Login Items and add the application. Let me know if it works, and if you have any feedback.