iMac OS 10.13.6 Trash Emptying is stuck

Hard Shutdown cured the lingering small horizontal window that reads: “Emptying the Trash… 3 items deleted.” Total Success! All is looking normal and working. Thank you very much for your assistance. At 80 I am one of those folks who came of age before personal computers and have been retired for 15 years so I really appreciate your assistance and that of BDAqua.

Can't. Machine does not respond to either Shutdown or Restart selection and, therefore I can't try Safe Boot from HD (holding Shift key down at startup. Shall I try a hard shutdown (on/off button) and then try the Safe Boot when attempting to do a fresh startup?

System: iMac. 2009. OS High Sierra 10.13.6.

Issue: Deleted most of the content on the external hard storage drive (Seagate Backup Plus Format Mac OS Extended (Journaled) and I believe it went to iMac Trash Bin.Unable to fully empty/erase Trash

Recap and New Actions:

Attempted to empty iMac Trash and process came to a halt and the following experienced.

Small horizontal window opened with message: “Emptying the Trash… 3 items deleted.”

Checked Apple Community and found similar issue with advice to upgrade OS. Having a 2009 iMac running OS 10.13.6 I was not confident upgrading would be successful.

Submitted Question Apple Community and received your advice to “Safe Boot from HD”.

Let iMac sit overnight before attempting Safe Boot and found the small horizontal window with message: “Emptying the Trash… 3 items deleted.” had disappeared. Also, items such as Mail, Firefox, etc. all worked normally.

Tried again the Empty Trash and got stuck at the same point as initially (2.a.)

Before trying a Safe Boot, I tried deleting each “backup” from Trash individually and then clicked on Trash and selected Empty,

At the erasing Trash point, the Question arose: “Are you sure you want to permanently erase the items in the Trash?”

I selected Yes.

The small horizontal box noted above appeared with the wording “Emptying the Trash…3 items present” and added above it was a second small horizontal box above it saying “The operation can’t be completed because the item “folders” is in use”.

Three Options were listed in the box: “Skip” “Stop” or “Continue”.

I tried teach Option got the following messages:

1) Skip: “The operation can’t be completed because the item “Library” is in use”

2) Continue: “The operation can’t be completed because the item “System” is in use”

3) Stop: The message “Emptying the Trash” came up in a new small box placed on top of the original small box and it contained the wording “3 items being deleted” and then that small box disappeared leaving in place the original small box present with the wording “3 items deleted” remaining in it.

At this point I am not sure what to try:

Safe Boot from HD to see if things clear when start emptying trash?

Try a hard shutdown to see if things clear when start emptying trash?

“Turn off” folders in some way so erasing of trash could proceed?

Further advice?

Yes, via Time Machine my iMac hard drive files are backed up to the external hard drive. Is that what you mean by trying to delete such files "via Finder?" Does that in turn mean when I opened the external hard drive and selected all backups for deletion that they instead were sent to the computer's trash and when I try to empty them from the trash I am doing it "via finder"?

I could reformat the external drive, except for the fact that the only items now present are backups remaining after all of the older ones got moved into the iMac unit's trash. I'm stuck trying the get them out of the iMac's trash and deleted.

Can you assist with advice on how to get those old backups out of the trash? Can they be returned to the external drive in some way and then I could reformat that drive and start backups fresh?

Excellent recommendation. It worked, with one little small issue remaining - the small horizontal window that reads: “Emptying the Trash… 3 items deleted.” I can't close it. How can I get rid of it? Tried to attach a screen shot but it won't populate into this message.

Neither Restart nor Shut Down functions work, only Sleep. Try a hard shutdown?