Why do some recent files NOT appear when right-clicking the Word/Excel icon in the taskbar?

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Windows Central Question

I have Word and Excel pinned to the taskbar. In Windows 8.1, right-clicking always showed recent (and open) files - so that I can pin them to my "pinned" list which appears above "recent".

In Windows 10, recent and open (!) files do not always appear in the right-clicked list.

(Interestingly, if I open a file from the cloud/OneDrive, the file name does - at least sometimes - appear in the right-click list. But I don't want to pin that one obviously - it's very slow.)
 

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