Hi @Aaron! Thank you for reaching out!
Sorry for the trouble here and confusion here. As you have mentioned, when sorting by due date it only sorts in one direction - oldest (top) to newest (bottom). This is currently the expected behaviour rather than a Bug.
I completely understand your point regarding the icon and I’m sorry to hear this is inconvenient for your workflow. There is an existing thread requesting this functionality. In case you haven’t yet, I would recommend you to upvote it: Sort by Due Date - ascending or descending option
Sorry again for the inconvenience! Please let me know if there is anything else I can help you with!