Cortana does do this, and there's actually nothing in the article that indicates that it wouldn't have worked perfectly well if he'd just hadn't done anything a

Cortana does do this, and there's actually nothing in the article that indicates that it wouldn't have worked perfectly well if he'd just hadn't done anything and let the automatic tracking do its thing. The real WTF here is not so much that it has a bad UX for manually entering tracking numbers (that's obviously not ideal, but IMO semi-reasonable given it's a fallback corner case) but that they pushed/spammed a notification that dumps you into the bad manual UX.