Q: Can't delete word document in trash

Quit the application(s) in which you opened the document, which may be Google Drive itself. Otherwise, log out or restart the computer.

Be sure there is not an icon app on your desktop related to the download.  If there is drag to trash then retry to empty trash.

Please read this whole message before doing anything.

The purpose of this procedure is to determine whether the problem is caused by third-party software that loads automatically at startup or login, by a peripheral device, by a font conflict, or by corruption of the file system or of certain system caches.

Disconnect all wired peripherals except those needed for the test, and remove all aftermarket expansion cards, if applicable. Start up in safe mode and log in to the account with the problem. You must hold down the shift key twice: once when you turn on the computer, and again when you log in.

Note: If FileVault is enabled, or if a firmware password is set, or if the startup volume is a software RAID, you can’t do this. Ask for further instructions.

Safe mode is much slower to start up and run than normal, with limited graphics performance, and some things won’t work at all, including sound output and Wi-Fi on certain models. The next normal startup may also be somewhat slow.

The login screen appears even if you usually login automatically. You must know your login password in order to log in. If you’ve forgotten the password, you will need to reset it before you begin.

Test while in safe mode. Same problem?

After testing, restart as usual (not in safe mode) and verify that you still have the problem. Post the results of the test.

This procedure is a diagnostic test. It makes no changes to your data. The instructions must be carried out as an administrator. If you have only one user account, you are the administrator.

Please triple-click anywhere in the line below on this page to select it:

sudo lsof | grep Trash | pbcopy

Copy the selected text to the Clipboard by pressing the key combination command-C.

Launch the built-in Terminal application in any of the following ways:

☞ Enter the first few letters of its name into a Spotlight search. Select it in the results (it should be at the top.)

☞ In the Finder, select Go ▹ Utilities from the menu bar, or press the key combination shift-command-U. The application is in the folder that opens.

☞ Open LaunchPad. Click Utilities, then Terminal in the icon grid.

Paste into the Terminal window by pressing the key combination command-V. I've tested these instructions only with the Safari web browser. If you use another browser, you may have to press the return key after pasting. You'll be prompted for your login password. Nothing will be displayed when you type it. Type carefully and then press return. If you don’t have a login password, you’ll need to set one before you can run the command. You may get a one-time warning to be careful. Confirm. You don't need to post the warning.

If you see a message that your username "is not in the sudoers file," then you're not logged in as an administrator. Log in as one and start over.

Wait for a new line ending in a dollar sign ($) to appear below what you entered.

The output of the command will be automatically copied to the Clipboard. If the command produced no output, the Clipboard will be empty. Paste into a reply to this message.

The Terminal window doesn't show the output. Please don't copy anything from there.

If any personal information appears in the output, anonymize before posting, but don’t remove the context.

Before you moved it to the Trash, was the file in your home folder? When you tested in safe mode, was Google Drive running?

Did you tried with Clean My Mac? Helped me a lot with bugs with the Trash, mostly fonts not installed, unused docs, etc.

There's a Trash Cleanup menu, where you can check your HD Trash and clean it, pretty simple. There's a free trial.

Also did you check in Mail app if there's no draft with the doc attached?

b5241 wrote:

 

Is Clean My Mac reliable?

No.

Absolutely do not install "CleanMyMac." It's a scam.

Please run the following command in the same way as before and post the output:

ls -@Oaen .T* | pbcopy