It seems that booleans option no longer works. I’m not sure if it was when I went to pro or not. I always end up joining shapes the long way.
In order for Booleans to work the following conditions must be met:
- each path must be closed (shows as black, not magenta when on the Default layer (or other layer set to show as black))
- the objects must overlap/intersect
- the objects must not be in the same group (this would be indicated by all having a dashed highlight)
Upload the file you are having difficulty with and a screen grab showing the selection state you are having difficulty with.