That box is checked. As mentioned it does show recent items for Internet Explorer. So it is working for that, but not Explorer. Your mention of Disk Cleanup clearing it made sense until I thought about Internet Explorer icon and how it is displaying recent items and also why as I have been opening things right now in Explorer it isn't showing under recent. I also opened a Word document and it does now show under recent. So it seems it is Explorer not working properly.
More experimenting. Now the folder I opened for the Word document does show under Explorer recent. But why not things like Pictures, and other things I open directly from Explorer. I must be doing something wrong.
edit: I unchecked the box "store and display...taskbar" and all recent items disappeared. Now they come back for Word. But not Explorer and so far IE.
Searching around I found that there could be corruption and saw this fix:
The issue may happen because one of the Jump Lists’ recent items in automaticDestinations hidden system folder is corrupted. Delete or clear Jumplist recent items in Windows 7 that is corrupted in AutomaticDestinations-hidden system folder is the likely solution.. To resolve and fix the issue, follow these steps:- Open Windows Explorer
Type or copy and paste the following into the address bar: %AppData%\Microsoft\Windows\Recent\AutomaticDestinations - Identify files that are comparatively larger in size than the rest of the file, such as files that have file size of 1 MB or more. Delete the abnormal file.
Another solution took it one step further: There is one other location that may have a corrupted file that is causing this problem. Make sure that all programs are closed. Open Windows Explorer, paste the following path into the Address Bar and press Enter. %AppData%\Microsoft\Windows\Recent\AutomaticDestinations Select and delete all of the files in that folder. Perform the same procedure on the following folder. %AppData%\Microsoft\Windows\Recent\CustomDestinations This will completely reset all of the Taskbar Jump Lists. Exit and reboot the computer.
I think it may be working but I am not doing something right. So I'd like to figure it out before I do this. Thanks