Apple - System Integrity Protection prevents Trash from being emptied
- Shutdown your laptop.
- Press Command + R and then the power button to boot into recovery mode.
- Click the Utilities menu and select Terminal.
- Type
csrutil disable
and press return. - Close the Terminal app and restart out of recovery mode.
- Login to your machine normally and launch the Terminal app on your Mac by either searching for it in Spotlight or locating it in the Utilities folder under Applications.
- In Terminal enter this command
sudo rm -rf ~/.Trash/*
it'll ask for your login password. That should clear your trash.
If that worked re-enable SIP.
- Shutdown your laptop.
- Press Command + R and then the power button to boot into recovery mode.
- Click the Utilities menu and select Terminal.
- Type
csrutil enable
and press return. Close the Terminal app and restart out of recovery mode.