I have achieved this by placing a board cutout over a pad on the bottom layer. This conflicts with my design rules, but I thought it might not matter. The board in the 2D view looks like this:

This is how I want it to look. However I am not sure if the conflicting board cutout and pad is acceptable.
After exporting the Gerber and seeing the view in the order page - this view does not show the cut outs at all, is this normal or have I done something wrong?

Thanks!
Chrome
109.0.0.0
OS X
10_15_7