How to Solve the High Sierra Bug – Can’t Move Files to Trash

delete files macMany members of the Apple community use the Trash folder of their MacBooks and Macs as a temporary service area for lodging their files with the possibility of deleting them later. However, there is also a type of Mac users who prefer the immediate file deletion. Such users are considerably inconvenienced by a reemerging prompt that reads “Are you sure you want to delete ‘filename’?”


The issue is especially pressing for those Mac owners who back up their data regularly and do not afraid to erroneously delete important files. The article aims to provide Mac users with simple instructions on how to get rid of the deletion alert, thereby making it possible to remove files instantaneously.

Possible Root Causes of the Problem

There are several causes of the reemerging deletion alert:

  1. A user attempts to delete files from external storage devices or network volumes;
  2. A user is not the Owner of the Home folder;
  3. A user does not have the Sharing and Permissions or Read and Write Privileges;
  4. The Trash directory has been removed;

Ways to Solve the Issue

Typically, these issues can be resolved by ensuring that a user is the Owner of the Home folder and has both Sharing and Permissions and Read and Write Privileges. As for the first cause of the issue, there is no workaround for it because macOS developers have made this design choice to ensure that users do not lose important files from the removable media by accident.

To change the Home folder’s owner:

  1. In the Finder, click on the Go tab;
  2. Select the Home option from the drop-down menu to access the Home folder;
  3. Once in the folder, use the Command + I keyboard shortcut or click on the Get Info option in the File tab to open the Info window;
  4. Enter administrator login details in a window that appears after clicking on the lock icon;
  5. Find an owner’s name in the Name column (to create a new owner click on the + button);
  6. Click on the Action menu and select the Make “User” the Owner;
  7. Close the Home

To change the Sharing and Permissions as well as Read and Write Privileges settings:

  1. In the Finder, click on the Go tab;
  2. In the drop-down menu, select the Home option to access the Home folder;
  3. Once in the Home folder, use the Command + I keyboard shortcut to open the Info window;
  4. In the window, use the disclosure widget to enable the Sharing and Permissions

(If a lock icon appears, click on it and enter administrator login details);

  1. In the Name column, select a user and choose the Read and Write Privileges from the list of available options;
  2. Apply permissions to enclosed items in the Home folder by clicking on the Action menu in the Info window and selecting the Apply to Enclosed Items option;
  3. Close the Home

Note that it is possible to undo any changes introduced to the Sharing and Permissions by simply clicking on the Action menu in the Info window and choosing the Revert Changes option.

To verify that the Trash directory has not been removed:

  1. Open the Applications and then proceed to the Terminal through the Utilities folder;
  2. In the search bar, enter verbatim the following command: ~/. Trash;
  3. Press Enter;
  4. If the Terminal response states that no such directory exists, then log in and out of your account and restart a computer.