When right-clicked my Windows Explorer icon in the taskbar only displays "Desktop" under "Recent". I use it to open lots of things, how come I never see them listed under "Recent". I guess these are called Jump Lists. They also don't display at all for Microsoft Word. There are some there for IE but they don't seem like my most recent visits. Are my jump lists messed up? This example is from a tutorial.
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.
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.
I am thinking I do not know how to use Explorer correct. Because now somehow Desktop and OS (C: are listed in recent when I right click the Explorer icon on the task bar. But other things I open are not in recent. The ones I think of specifically are pictures and music. I open those all the time but they don't appear under recent.
Easiest way to get a folder to show up in your Jump list (assuming it is working) is create a text file in that folder and open it and then close it. If that doesn't work try adding some text and saving it.
This always works for me when I want to pin a folder.