Bought a ticket 3 weeks ago, F was wide open on the 2-segment outbound journey. Applied a regional upgrade online to be waitlisted.

About a week ago, the first segment upgrades. But the record becomes out of sync, with the 2nd flight appearing before the 1st in the record. Called UA to get it back into sync and see what's up with the 2nd segment upgrade. Get a "that's wierd, the second segment isn't waitlisted" response from the agent who fixes the sync issue and gets the 2nd segment waitlisted.

Yesterday, at the 24 hour mark, 4 F seats remaining and got an online check-in buy-up offer of $69 to clear to F on the second segment. Immediately call UA to see why the upgrade didn't clear. After waiting for 35 minutes on hold, I get disconnected. I call again later...and after a 20 minute wait, I get an off-shore agent who says there's no sign of a waitlist on the 2nd segment. He has problems adding in the upgrade request and needs to put me on hold for 15 minutes so that he gets help.

After the help, he says he's successfully added the segment to the waitlist and there should be no problem clearing.

Get to the airport today. Check-in bag and offered $69 upgrade again for second segment. Ask ticket counter agent (EWR Premier Access) what's up; she says there's no record of the second segment upgrade request being made. She says the gate agent would be able to fix it. Another passenger checking in at the kiosk next door sees his reservation messed up and starts yelling at the check-in agent; they both leave the area. Went to another ticket counter agent in the Premier Access area who said "wow, there's no record of the segment being waitlisted, and I'll need to call our help desk to fix it." She points out one seat remains and the call should fix it.

In the 15 minutes the ticket counter agent is on the phone waiting for help, the last remaining F seat is sold.

Thoughts??