Moving File(s) to Trash permanently deletes, do not go to Trash.

Let's try.

First, we need to remove this file.

1) Paste this command into Terminal:

sudo rm ~/.Trash

You will be asked to type your password. Type it (nothing will appear as you type, not even asterisks or bullets) and then press enter.

2) If this succeeds, then we can proceed to the next step and recreate the directory.

Paste the following line in Terminal:

mkdir ~/.Trash

3) To see if this worked ok, paste the following command (it is the same that you did before to check the settings of .Trash):

ls -lda ~/.Trash

and post the output here.

Also, at this point you can try dragging something to the trash and see if it is now working.

Moving a file to the Trash does not automatically delete it until you right-click on that Trash icon and choose Empty Trash. This particular dialog that you show is the result of selecting that functionality in the Finder's Preferences > Advanced panel, and if you click Delete on that dialog, then the Trash is emptied.

This usually indicates that you lack proper access to the Trash folder.

Where are the files that you are trying to trash? Somewhere inside your home folder - eg. inside your Desktop, Documents, Pictures, etc?

When dragging to trash, these would go to a hidden folder inside your home folder.

Files that exist out of your home folder (e.g. in /Applications) would go elsewhere.

I will assume that it is files in one of your folders that you are trying to delete.

Open Terminal, type the following line and paste the output here for us to see:

ls -ld ~/.Trash

This tells us that you have NO permissions to access this, which explains why you are unable to move things to the trash.

Also, this looks like a regular file, and not a directory.

I don't know how this came to happen, but we need to delete this file, and create a directory with proper permissions.

The default permissions on a folder that you create via mkdir will be drxr-xr-w or 755 or user=read, write, search/execute, group=read, search/execute, and other=read, search/execute. The original permissions on that ~/.Trash folder created by the operating system is just 700, or user=read, write, search/execute and no one else has any permissions.

In the Terminal, you can set the correct permissions on that Trash folder and see what you have set:

chmod 700 ~/.Trash
stat -f '%Sp%t%N%n' ~/.Trash

There are no special access control list settings (ACL) for it.

You need to confirm this by typing

y

Good point, VikingOSX. I had forgotten that part about fixing the permissions once the directory is recreated.