WPF context menu bound to List dependency property?

As you suspected, your problem does seem to be caused by the use of List.

I don't see why you've made FooList a dependency property. You're not making it the target of a binding, which is the most common reason to create a dependency property. You haven't implemented a callback, so it can't do change notification (the second most common reason to create a dependency property).

You're not using it for value inheritance. So why, then?

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