Okay, I think the issue is that you’re using a Button.
If you have a border that has visibility: visible, then the EntryWidget detects clicks by default, and informs the Listview about clicks, and so those events fires too.
With a Button however it kind of consumes the click event [probably using wrong terminology here] so the EntryWidget is never informed about the click.
This is true for any UserWidget, not just EntryWidgets. If you have a widget with a border and override the widgets OnMouseButtonDown function, you can see that it fires when you press the widget. If you then but a Button on the border, then OnMouseButtonDown no longer fires when you press the button.
Either you keep the button but need to implement your own logic, binding to dispatchers helps in this aspect. See the last parts of the TreeView titled Treeview - Don’t change expansion [Override click method].
Or get rid of the button. I ofc don’t know exactly what your individual tile is supposed to do, maybe there’s a good reason to have a button, but for a simple inventory the button just complicates things.