My external hard drive trash won't empty

Here's is what I just did to get files/folders deleted from my external hard drive connected to my iMac, using terminal:

First, drag the external hard drive file/folder into the trash. It should now appear in 'Trash' when you open it up in a finder window.

Now, change directories in terminal to your external hard drive (cd space and then drag your connected external hard drive into terminal and that will complete the path). Confirm you have changed directories by simply typing the following in terminal:

ls

Next, type the following command in terminal and include a space after:

sudo rm -R

Finally, drag the file/folder from trash into terminal after the command above that you've just entered. the command will look something like the following (includes the path to your external hard drive 'trashes' even though the files appear to be in your computer 'trash'):

sudo rm -R /Volumes/nameOFyourEHD/.Trashes/501/nameOFyourFileOrFolder

You may or may not be asked for your administrator password due to using 'sudo'. Enter your password if prompted, obviously.

Terminal may sit there for a few seconds blinking or return a long string like: override rw-r--r--t

and ending with ?

I just held down return through all the long strings ending with ? until terminal was back at my proifle bash:

my computer: my computer profile$

If the file you dragged from trash into terminal isn't removed after a few minutes, whether you get long strings ending with ?, or not, close terminal and start from the beginning. (my new iMac is much quicker and a better machine for this than my 2010 macbook that sometimes doesn't respond as well, probably from my own user error(s)

In my case, I am deleting time machine backups so there's a lot, which takes some time and the external hard drive will need to stay connected to the computer during this time.

Several times now I have followed the steps above to delete external hard drive file/folder.

I followed this step, and it wiped the trashes of my external, however, the drive did not free up any space when it should of freed up a few hundred gigs. Trying to do some cleanup using Disk Utils, but I'm concerned now...

Did you ever figure this out? I'm having the same sort of issue right now. Tried to delete some back ups from my Seagate External Hard Drive and now they won't delete fro the trash... they also disappear when I eject my hard drive. Super weird!

Try restarting your MBP. Nothing in the trash should be being used after a restart.

well, I didn't memorize all the methods in the forum and I don't know you have seen them all. 😎

Try this… Open the trash and do a select all, right click on one of the files and select delete immediately, Assuming you haven't done that one. 😁

Trash – Empty When File is Locked or in Use

Try holding down the option/alt key while trying to delete the Trash. If that doesn’t work, here is some more information.

Trash FAQ

Trash won’t empty

FWIW, renaming the files is a bad idea. OSX wouldn't be able to locate the files on the external drive since they would have different names.

What is this an external bootclone ?

you could try this…

in the Terminal type or copy and paste

sudo rm -R

add a space after the R. Drag one of the locked folders that are in the Trash into the Terminal, hit return. Enter your password, hit return.

Post the results.

Can you right click on the external drive and post a screenshot of the "Get Info" panel?