I learned that if you use miles/copay and then board because they said they'd get you, then your chances of upgrading are close to 100%. They got CKs and SWUs users but passed me over to a ExPlat lower on the list relying on complimentary upgrades because the said they didn't have time to process the copay if I've boarded. In spite of telling me they'd get me.
I argued (not loudly), escalated (was lucky a supervisor gate agent came on board), argues more, and finally got it (I said if you are giving it away because of time constraints, I'm also eligible for free upgrades). I was #7 on the list, I saw on the app #9 cleared, and that's when I got up to speak to the gate agent who just came on board.
I got it because 5&6 didn't want to split up, so I cleared. But it's a tough choice - give up your upgrade or give up a place to put your carry-on.
If it clears prior to gate control, the payment is automatic, why not at the gate?