RealSting

Ahhh... thank you very much. It's not obvious as when I used Illustrator I didn't have to do this! Thank you again. Can i leave this in Layer > Fill Mode > Alternate (Even-Odd) mode?

I have attached the .afdesign file. There is a texture applied to the background square which may or may not show up on your machine, though texture or not, didn't make any difference to the problem on my machine. I'm using Mac OS 11.6 on a L2013 MacPro, 32GB RAM, D700 Graphics. Thank you. Test.afdesign

Yes, I've tried converting it to curves. Im now doing the same and now the square is working but the circles are not!!! Its a bug! If you look carefully at other attempts in the layers panel in the video I've attached here, you'll see it did work at one point. But it then stops working. I also tried it without any texture fills and/or strokes. Thank you kindly to everyone for your responses. AD2.mov

Please see my updated link above. Thank you. This behaved differently.. I was able to make a cut out with the rectangle in my earlier attempts but not with the circles on the screen.

Yes, all the layers were selected. I’m not a newbie to this game.. been doing it for decades on Adobe and others. This is definitely a bug! No doubts, because the operations outcome is erratically different though I’m doing the exact same thing each time. It either works or it doesn’t.. it doesn’t (reliably). I’m surprised there are issues with these fundamental functions - illustrator never gave me these issues.. it just worked! UPDATED - See Video link below: https://youtu.be/lS27xv58Kr0

Attempt 1: Ive created a large Square using the rectangle tool, filled for my background. I place 3 smaller circles in it plus a smaller square. I select all of the smaller shapes inside the large main background square. I select the Subtract boolean command. Result? The three circles are cut of out the background square but the smaller square is not!! Attempt 2: I create the same background square in a new project as in Attempt 1. This time I just place a smaller square (as in Attempt 1) into the large background square. I select subtract tool as I did in Attempt 1 to cut out the the small square. This time it worked! But now Adding the circles as I did in Attempt 1, do not cut out!! WTF!!! The boolean operations - especially subtract, don't make any sense in Affinity Designer!