Trash problems may periodically crop up for OS X users, mainly because of permissions issues that prevent a user either from accessing files in the the trash folder, or from accessing the folder itself. When this happens, you may see problems such as files deleting immediately without going to the trash, deleted files reappearing in the trash, or files persisting in the trash and not deleting (sometimes without an error message).
Trash folders are hidden folders that are in one of two locations: either at the root of a mounted drive (called ".Trashes"), or in the user's home folder (called ".Trash"). When you move a file to the trash, if the file is on the same drive as your home folder it will go to the ".Trash" folder in your home directory, otherwise it will be moved to the ".Trashes" folder at the root of the drive it's residing on.
To test which folder is being used, if you have files in the trash, unmount any external drives you have attached to your system. If the files disappear from the trash, then they are residing in the ".Trashes" folder at the root of the drive and not the ".Trash" folder in your home directory. With this information, you can go about fixing trash issues by removing the appropriate trash directory.
Files in the home folder
If you've determined the files are in the home directory's trash folder, then you can use the following command in the Terminal to remove the directory and all files in it.
sudo rm -rf ~/.Trash
Files on other drives
If the problem is with a trash folder on an external volume, you can remove it with the following procedure:
type this command followed by a single space (do not press enter):
sudo rm -rf
Drag the external volume to the terminal window
Delete the final space and complete the command with ".Trashes" so it looks something like the following:
sudo rm -rf /Volumes/VOLUMENAME/.Trashes
After these commands are run, you can recreate the trash folder by logging out and logging back in, and the trash should behave normally again. Keep in mind that mounted network shares (including those from networked attached storage devices) will not use a trash folder, and instead will only have the option to remove files immediately.
WARNING: Be very careful with the "sudo rm" commands, and be sure the syntax is exactly as we show here. Misuse could result in lost data, and potentially an unbootable system.