Thanks for the question. I understand you are experiencing issues moving items to the trash. Based on the symptoms you described, it sounds like one of the following solutions may resolve your issue:
If you can't empty the Trash or move a file to the Trash
For example, this message might appear when you try to empty the Trash: "The operation could not be completed because the item '(item name)' is locked."
First, try holding the Option key as you choose Empty Trash from the Finder menu.
Otherwise, check for these conditions:
- Is the file locked?
If files are locked, unlock them before deleting or delete using the tips in the "Deleting locked files" section below. Also, see this article.
- Do you have correct permissions to modify the file?
Every file and folder in Mac OS X has some permission settings to help define what you or other users can do with the file or folder, for example whether you may modify it or not. If see an alert box with a message that says you do not have "sufficient" privilege or permission, see the tips in the "Emptying the Trash" section of this article.
- Does the file or volume have special characters?
Usually, Mac OS X can delete files whose names contain special characters, but sometimes you might need to follow this advice.
1. Note the name of the volume which the files are being deleted from. If you are not sure of the item's location, you can verify that by selecting it then choosing Show Info from the File menu. If the name of the volume contains any special ASCII characters, such as a bullet or trademark character, temporarily rename the volume so that it does not contain these characters.
Example: If you cannot delete files from a volume named "·Dox", rename the volume to "Dox". After the Trash is empty, restore the volume's original name as desired.
2. Examine the name of the files or folders you cannot delete. They should not contain a solidus ("slash", "/") character or any other special ASCII character such as a trademark, quotation mark, or copyright symbol. If the file does, remove the special character or slash from its name, then delete it.
Example: If you cannot delete a file named "Things/stuff·", rename the file to just "t", then delete it.
For additional information, see the full article: