I think you may have a couple of corrupt .lnk files in your Recycle Bin. The Securely Empty function is trying to open those files (to overwrite their inner contents with random garbage) and can't do so, as shown. If you can delete them manually, I'd suggest you do so, as they're unlikely to contain anything sensitive. If not, you might need a CHKDSK or similar, as seems you have some disk errors
(PS: yes, I checked the Securely Empty function on a random VM, and it worked fine...)
(PS: yes, I checked the Securely Empty function on a random VM, and it worked fine...)
