The top three items in the cut planner (Order by Layer, by Group, or by Priority) take precedence over the stuff below, for the most part. If you have ‘Order by Group’ on, it assumes you’re doing something like running a bunch of keychains, where each one is a group and needs to be treated as a unit before moving on to the next one. Similarly, ‘Order by Layer’ can also override the inside / outside path ordering.
Having the order overridden by one of these ‘master options’ or not having your shapes closed are the two reasons I’ve seen the inner / outer sort fail. It’s very predictable otherwise.