How can I get the tearoff menu to reflect changes in the regular menu?

At the moment torn-off menus will not reflect changes made to the original menu. This functionality is slated for an upcoming revision of the menu system in Tk. It's possible to do this now by tracking the associated tearoff using the -tearoffcommand option for menus.

This allows you to specify a command that will be executed when the menu is torn off. The widget names of the menu and tearoff menu (tearoffs are created as toplevels with the name .toplevel. Tearoff when torn off) are appended to this command before it is evaluated.

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