There are chances that due to some system error recycle bin stops functioning all of sudden. The windows error notification with the option to empty the Recycle bin does not help any more. What's more, each delete process is accompanied by an error. To solve this problem, manually delete the hidden system folder; it will be automatically re-created without errors by Windows.
You need to open a command line with administrative rights to access the system folder. To do this, type in "cmd" in the Start menu, click on the result "cmd.exe" with the right mouse button, and then select "Run as administrator". Confirm the User Account Control dialogue box. Now using the command line, change to the parent folder of the concerned drive.
In XP, the hidden folder is called "Recycler", and from Vista onwards "$RECYCLE.BIN". To make Windows show this folder, use the command "dir/a". If your system has multiple Windows installations, you might find both kinds of Recycle bin folders, but you must delete the one which belongs to the OS with the problem. For this, use a similar command: "rd /s /q $RECYCLE.BIN". Pay attention to the exact capitalization in case of the folder names, because the system will otherwise not find the folder. If the access is denied, it is possible that you do not have administrative access.
On the system drive, the Recycle bin is blocked by Windows and you must start the system in Secure Mode to be able to perform the described steps. Delete the relevant folders from all the relevant drives. Windows will re-create the Recycle bin folders when the system starts next and you can use it again.