Monster Widget is a bit of a trap like that. Despite how it looks it doesn’t actually place “real” widgets into sidebar.
It is a single widgets that creates output of other widgets inside of itself. If you are significantly interfering with its expectations then it won’t pick up on changes, since it’s not engineered to do it.
You will likely need to use its monster-widget-config filter to modify configuration, excluding native widget and splicing your own in.
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