Adding context menu and/or tooltips to existing menu

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I apologize if this has been asked before, but after a good amount of wasted time I think I've come to realize that adding a context menu to an existing Menu isn't possible.

I have a basic "File" "Edit" "Help" type Menu and I'd really like to add a context menus to them.

Does anyone know if a UDF for this ability has been created?

Also, I've had trouble getting tooltips to work with Menus as well. I found a UDF that enables menuitem tool tips but still not tooltips for the menus themselves. Thanks for any help.