Last week flying Portland to Washington-National airport via Chicago for work, I had a very strange experience with an upgrade that really wasn’t. 24 hours before my flight I checked-in online and noticed that I received an upgrade on Portland-Chicago. Great news! There were still a few seats open and I selected 1A. For my second flight, there were not a lot of good seats so I stuck with my bulkhead window.

On the day of the flight as I started to pack for the trip, I decided to look and see if any better seats had opened on my second flight between Chicago and National. That’s when I found my seats completely gone for both flights and if I tried to check-in again, an error occurred. I immediately called United as I was more concerned about not having seats than not being checked-in. The agent reselected my seats, confirmed I was in first class for the first segment and hung up. I was able to check-in with no issue and felt a little relief. I wanted to make sure everything was ok with my reservation so I logged onto United.com via my computer and sure enough, there was still an error telling me to call reservations.

The second phone call was a little more productive. The agent was able to see the problem, a note had been added by airport staff that first class may be oversold and that they would need to deal with it at the airport. I asked if she could preserve the seat choice I had made for the second flight and she stated that she could not but that they should be able to fix it at the airport. I finished packing and headed to the airport much earlier than I had originally wanted, throwing my afternoon plans with my wife off.

When I arrived at the United check-in desks and explained the issue, the agent saw the problem and called the gate. They stated that a first class seat was broken and that I was the only upgrade so I was downgraded. The check-in agent preserved my seat for the second segment but told me the gate would have to get a seat for me for Portland-Chicago.

At the gate the agent apologized and gave me a voucher for $250. That was definitely nice but led me to wonder what seat I was going to get as a result. The conversation after I said “thank you” went something like this:

Agent: hmmm, I can put you on a later flight to Chicago

Me: But then what time would I get to Reagan?

Agent: Oh, your destination isn’t Chicago?

Me: Uhhh, no. I have an hour connection to the last flight of the night to Reagan.

Agent: I see… Well, I can get you to Dulles at 1am by going through Denver.

Me: If there are no other options then I guess Dulles it is.

I was told later than I should have pushed harder at this point because it was painfully obvious that no one had actually looked at my full itinerary when making the changes and that’s what had messed up my connection seat selection. It was also obvious that the Portland-Chicago flight was oversold and this agent was looking for a way out.

The agent ended up giving me a middle seat from Portland to Denver and then first class from Denver to Dulles. She also provided me another voucher for $350. All told, the airline gave me $600 for the screw up and though I would have much rather gone to National, I was willing to put up with a late Dulles flight for the compensation.

Looking at the situation now I wish someone had paid more attention to my reservation when performing the downgrade. It would have saved them a little bit of money and me a headache. I also think they (United) got around the involuntary denied boarding by claiming ignorance about my connection and then offering me a different flight. Based on what I saw, they were out of seats completely in coach so there was nowhere to put me after the downgrade. In addition to that, I saw a young lady show up to the gate late and she was denied boarding since they had closed the door. So in reality, coach went out with an empty seat that I could have taken.

It all worked out but was a headache to deal with, especially having to get to the airport early to sort it out.