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Have a look at the gui.json file, and if necessary edit the dictionary values in there if you cannot do it through the gui itself.
The dialog will only appear if it does not find that plugin name already on a menu/toolbar. The idea being that when you upgrade you don't get nagged. So if you want to test with the gui box part make sure the plugin is not on any of the four menus/toolbars, and then do Add plugin.
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