I believe that the HoverImage and PressedImage properties of ImageButtons inside a BillboardGUI don’t work in any situation. It does work for ScreenGUIs but not for BillBoardGUIs.
When put in a BillboardGUI:
These are the properties of the ImageButton inside the BillboardGUI:
As you can see, the HoverImage and PressedImage both have a proper value.
It doesn’t seem like it’s a major problem. It’s possibly a bug. I’d maybe experiment around with it for a while and see if anything else can fix the problem. 
BillboardGuis in the workspace don’t process user input, only ones in the PlayerGui. Where are yours parented?
Ohh. It’s parented in the character you see there.
Shame it doesn’t process the user input. Is there a work around for this?
Edit: WHOOPS! I found out I should use Adornee for that 
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