VSTO Ribbon Context Menu Dynamic Hierarchy

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How does one create a dynamic menu hierarchy using VSTO Ribbons (for Outlook 2016)?

The xml placeholder could look like this, but I need to add/remove a menu tree under the menu root (instead of dummySingle). It seems like there would need to be something like a "getDependents" callback for menu items.

<?xml version="1.0" encoding="UTF-8"?>
<customUI xmlns="http://schemas.microsoft.com/office/2009/07/customui" onLoad="Ribbon_Load">
  <contextMenus>
    <contextMenu idMso="ContextMenuMailItem">
       <menu id="Menu Root" label="Menu Root" >
        <button id="dummySingle"
            label="dummy"            
            onAction="DummyAction"/>            
      </menu >      
  </contextMenus>  
</customUI>
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