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Mac OS X can sometimes throw permissions errors when trying to delete files or empty the Trash. First: Try quitting all apps to release the file lock or permissions, then attempt to Secure Empty Trash by holding down the Command key and right-clicking the Trash icon. Now you can try emptying the Trash as usual through the Dock, a keyboard shortcut to dump the file, or go the rm route mentioned below.
If that still doesn’t work you can try the ultimate delete approach using sudo and -rf *. Using sudo requires the administrator password but combined with rm it will absolutely forcibly remove any file regardless of whats going on with it. Good job Trevor, even the guys at the genius bar here in Naples didnt know that trick:-) worked perfectly! I have tried everything as well … And this was the ONE thing that completely erased my Trash Box!
I have tried EVERY tip before and this is the only thing that would completely empty my trash. I tried every method I could find and couldn’t get rid of a locked file deleted from Time Machine.
Command, option, shift, and right clicking the trash to secure empty worked for me too…there aren’t enough thank yous to go around!
Finally had enough and went the dangerous route… with the sudo rm -rf option and STILL I got the same thing. If you don’t want to format the pd then just take all the items from trash and delete those in some other os like windows.
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I got my first Mac about 16 years ago and even though I always try to focus on what first time Mac users need to know, I still forget to periodically review some of the basics.
There are three ways to discard items to the Trash, which is represented as an old fashioned trashcan. The Trash in OS X is located on the Dock, which comes by default on the bottom of your screen. Should you wish to retrieve something from the Trash prior to emptying it, just click once on the trashcan icon. If you are particularly concerned about security, then you can make items deleted from the trash mostly* un-recoverable by choosing "Finder > Secure Empty Trash" from the menu bar. As you open applications (or open files to launch applications), their respective icons appear in the Dock, even if they weren't there originally. The Dock keeps applications on its left side, while Stacks and minimized windows are kept on its right. When you quit an application whose icon resides in the Dock (such as Safari or Mail), the illuminated activation light disappears, but the icon remains.
Note: Control-click or right-click a Dock item to see a contextual menu of additional choices, including open windows.
TweetEmailYou can trash any file in Mac easily by just dragging the file to the Trash Bin icon.

Mac OS might warn you at this point that the file you’re planning to trash is locked, or contains locked items. Move the desktop folder that you renamed to your disk, to replace the folder that you trashed. When you click the Trash Bin icon, you will see its contents displayed on your screen.
Locate a screw-like icon at the top of the trash bin screen and open the drop-down menu next to it. If you don’t want any undelete software to recover the files that were in the trash bin, you can secure empty your trash. In the Finder tool, open the Finder menu, select the Secure Empty Trash option, and click Ok when prompted to confirm. If you’ve got some files that you want to permanently delete from your Mac, then you need to read this! But much like when you put garbage into the trash bin at your house, those files will just sit in the trash bin until you empty the trash.
Well, what you might not have realized is that even after you empty the trash, those files are still not really gone! Even though you empty the trash, and you can no longer see or access the file, a person with enough computer knowledge and ability will still be able to retrieve that file from your hard drive, since the data will still exist on your hard drive until it is written over with new data. The only way to prevent this and make sure that your files are really deleted is to Secure Empty Trash.
When you secure empty trash on your Mac, all of the files in your trash are written over with blank data, so that those files have no chance of being recovered.
For that reason, performing a secure empty trash is something you want to be careful with, as there really is no coming back from that, unless of course you’ve kept a backup copy of your files on a removable disk or time machine. If you found this article to be helpful to you, please let me know by clicking the “Thank You” button below, adding your comments, or rating this article using the five stars at the beginning of the article. I’m 27, and live on Long Island, NY with my beautiful wife, our dog and our beautiful new baby boy. This is intentionally not spelled out easily to try and prevent any novice users from accidentally deleting something significant. Subscribe to the OSXDaily newsletter to get more of our great Apple tips, tricks, and important news delivered to your inbox!
After trying Terminal and all the suggestions on another site trying to delete old Time machine Back Ups Command Option Shift and Delete the trash worked. I have been working for two days trying to delete locked files from the Trash on my iMac running OS 10.8. The fiolder in question is actually on an external WD hard drive, thus only show up in trash when I plug it in. You need a space between f and * but realistically if you can’t follow instructions then you absolutely should NOT be using the Terminal let alone the rm command with a * (anything) wildcard which can delete any and all files on your Mac without any confirmation. If you have files, folders, or applications in your Trash, the icon will be full of paper, as shown below. It primarily serves as an application launcher, but also has great tools for choosing specific open windows.

For example, if you want to listen to some music, click the iTunes icon (the icon with music notes) to open iTunes. That means if you've got a lot of applications open, your Dock will grow substantially. When you quit an application whose icon doesn't reside in the Dock (for example, you just finished playing Chess), its icon disappears from the Dock. If so, you might enjoy hanging out with other like-minded folks on the Mac Geek Gab Facebook Group. It’s very different from the way you’d do it on a PC; on a PC, you just right click on the Recycle Bin and select Empty Trash. It can be frustrating, trying to discover how to empty the trash bin if you don’t know the process. David is a software developer and technical writer with over 10 years of professional experience. Don’t risk having someone else find your sensitive data on your Mac, read on and I’ll show you how to secure empty trash so those files will never see the light of day again! If this article did not help you find the answer you were looking for, than please leave a comment, or send me an e-mail for further help, and I will be happy to assist you further! I have always had a passion for all things tech related, and that passion has provided me a great variety of work growing up.
We will cover two different approaches to this, the first changes a files flags to attempt to unlock the file in question, and the second is a no-nonsense force delete. When an application is running, the Dock displays an illuminated indicator light beneath the application's icon. If you minimize a window, the window gets pulled down into the Dock and waits until you click its icon to bring up the window again. It's really "left" and "right" of a separator line that appears near the far right of your Dock. To make any currently running application the active one, click its icon in the Dock to switch to it (the active application's name appears in the menu bar to the right of the Apple logo, as shown below). If you look closely, you'll see a vertical separator line that separates them, as shown below. I would advise not to use the terminal at all, just reboot your Mac and empty the trash as usual.
If you want to rearrange where the icons appear within their line limits, just drag a docked icon to another location on the Dock and drop it.
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