Okay I'm getting tripped up here. I thought GUI's overlayed themselves in declaration order. Heres a scenario
In this order these GUI's are made. BackgroundA (An ImageLabel) w/ ZIndex 1 BackgroundB(A TextBox) w/ ZIndex 1 and Main (an ImageButton) w/ZIndex1
Yet Background B gets on top of main. Is there any reason in particular this can happen?

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What are their parents? It's important to note that descendants will always have a "higher natural ZIndex" than their parents.