Trash borked

[MR_Boogy]

I did a big clearout on my Catalina machine, removing loads of files and apps. When I came to empty it it gave errors that a couple of items couldn't be removed as they were in use, so I cancelled. After a restart (or 5) I still cannot do it. I get the same error and if I stop/skip it then sits forever on "emptying the bin". I can't cancel this - it ignores the "stop emptying button". And I cannot open the Trash to see what's in there... only solution is to restart (again):

I've tried force emptying but I'm not sure if it worked (I use a PC keyboard without dedicated option key).
Is there some other way to do it? I must have 10s of GB in there.

BTW I've noticed it reported several GB can be "purged" on my drive. Is that the same as Trash or something else?

 

[velocityg4]

Any Windows keyboard should have a Ctrl, Windows and Alt key. Each of those was assigned the role of Ctrl, Command and Option in macOS. Some forward thinking manufacturers use a generic key in place of the Windows key. You just need to figure out which is which. You can also reassing the modifier keys in System Preferences > Keyboard > Modifier Keys.

Did you try doing this in Safe Mode. If the files are in use after restart. Something is being used by a process which runs at boot. Safe Mode will disable most startup items.

As you're removing apps and apparently one is starting which is using one of the deleted items. You need to clear out your startup items then restart. These are in:
- System Preferences > Users & Groups > "User" > Login Items
- ~/Library/Launchagents
- ~/Library/Launchdaemons
- /Library/Launchagents
- /Library/Launchdaemons
- /System/Library/Launchagents
- /System/Library/Launchdaemons

Notes: You may not have all these folders. Be careful and only remove the stuff you're sure of some may be necessary startup items. ~ Denotes the user folder. Some folders may be hidden. (Command-Shift-Period) to show hidden items.

If those don't work you can try these fixes.