Honestly, I dread this question 😅 It’s come up a few times over the years, and I cannot come up with an easy way to explain it. The “simple” explanation is that when a custom shape object is applied to a bone it inherits that bone’s orientations. So if you want the custom shape to be oriented a specific way, you need to match your custom object shape to the bone’s orientations.
….does that make sense? It’s not an easy concept to conceive via text, so I don’t expect it to make sense 😞
