Originally Posted by
mahasamatman
I tried to see how much it would be to upgrade YVR-DEN-ORD-DTW (no long layovers), and United said it would be 20 PlusPoints per segment. There may have been consideration for connecting flights before, but it appears that no longer exists.
I think you're reading the screen wrong. If you select each leg, it should still only total 20. You'll be charged the highest amount of any of the legs that clear. In your case, if you select all three, you'd be charged 20 if any of them cleared -- even if it was just ORD-DTW. There's even a big note to that effect on the selection page:
The amount of PlusPoints we deduct will be equal to the highest-priced upgrade you request. We’ll deduct this amount as soon as we confirm your first upgrade. Once you complete all flights in your upgrade request, we’ll refund the difference between what we deducted and the highest-priced upgrade you received, if applicable.