Can't add button to my auto layout navigation menu

I’m trying to place a button inside an auto-layout nav menu but the blue mark for auto-layout isn’t appearing. I feel like I’ve done this many times and it’s not working for some reason. It works for fonts but not my created button. Does anyone have any idea why and how I can fix it? I’ve linked a video above to show the problem.

Hold Cmd/Ctrl while moving an object. Or reorder the layers in the Layers panel.