The ListBox (or, to be specific, the ScrollViewer within the listbox) clips any adorners attached to it's children. This is done to ensure that adorners for items scrolled out of view are not shown. To get around this, you need to explicitly put thing in the Window's adorner and not that of the listbox or listboxitem.
Another option I thought of is to take away the scrollviewer clipping, by using a StackPanel for my items instead of a ListBox. – CitadelCSAlum Feb 17 at 15:22 1 I have been able to solve this problem. I have shown the code I replaced above.
Thank you for pointing me in the right direction! – CitadelCSAlum Feb 17 at 16:09.
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