Well, for the Office clipboard to display "automatically" as the option in the task pane says, you'll need some sort of a trigger. My first guess was that you have to copy items, say, three times—but it doesn't seem to work like that.

The Windows clipboard only contains the items you last copied (or cut).

On the other hand, the Office cipboard, represented by the task pane, may contain several items recently copied or cut. By default, items are only collected to the Office clipboard when it is displayed, and you can display it by clicking the dialog launcher button in the Clipboard group of the Home tab.

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Stefan Blom
Microsoft Word MVP

Microsoft 365 apps for business
Windows 11 Professional