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The Pitfalls of Applying Upgrades to Flights Purchased With Points

Feb. 22, 2018
8 min read
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While many points and miles enthusiasts opt to book premium award flights using airline miles, there are others who derive benefit out of booking "paid" travel with flexible currencies like American Express Membership Rewards points, Chase Ultimate Rewards points or Citi ThankYou points. As TPG has discussed before, a helpful benefit to booking flights with these flexible currencies through their respective travel portals is that the itinerary more or less functions as a paid flight — meaning the passenger earns elite-qualifying miles and dollars, as well as redeemable miles (albeit sometimes at different rates).

In addition, it's even possible for elite travelers to apply upgrade certificates — such as American Airlines systemwide upgrades, or "SWUs" — to these flights booked through Amex, Chase or Citi travel portals. But beware: Once you apply an upgrade, you might lose any flexibility you'd otherwise have in changing your ticket, even if it's within the airline's normal cancellation window. As an example, I'll share my experience using Citi ThankYou points to book a "paid" flight on American Airlines, which I then upgraded using an SWU.

Booking, Take 1: July 2017

Over the summer, I was looking for some fun mileage run opportunities on American. I had some American SWUs to burn, so my plan was to find one of the longest flights I could find on AA metal (so that I could use an SWU, and so that I could get at least 1 elite-qualifying mile per mile flown). I also have a good friend from school living in Hong Kong whom I hadn't seen in years, and I decided I'd try to get out there to see him. I was able to snag a one-way flight from New York (JFK) to Hong Kong (HKG) via Los Angeles (LAX) (where I'd get to spend hours in the glorious Qantas First Class Lounge!) for only $420, and made separate arrangements for my return to New York.

This was all before the massive Citi ThankYou devaluation in late July 2017, before which I could redeem Citi ThankYou points at a rate of 1.6 cents per point as a Citi Prestige cardholder (the redemption rate is now 1.25 cents per point). So I used approximately 26,250 Citi ThankYou points to book my flight. I'd also been monitoring upgrade inventory on my flights using ExpertFlyer (American uses the "C" bucket for upgrades from economy to business class), and was able to call American and confirm an upgrade by applying an SWU to the LAX-HKG leg. Alas, confirmable upgrade inventory on American's premium transcontinental routes was, and remains, paltry.

Unfortunately, the evening that I booked my ticket, a work obligation came up — so I began working to cancel my ticket. First, I called American, and after a longer-than-usual wait, they were able to undo my SWU (though I would ultimately have to call to have them redeposit it to my account).

Second, I called Citi — and started running into serious problems. By the time I was able to call Citi, it was 11:30pm the night after I booked my ticket. Citi representatives have explained to me that for refunds of flights booked with Citi ThankYou points, Citi follows the rules of the particular carriers. For American, this meant that I could cancel any time before 11:59pm the day after I purchased my ticket. So basically, I called Citi with 29 minutes to spare, thinking that would be sufficient.

It took forever to get to the right person. I called the Citi Prestige concierge first, who transferred me to someone at the Travel desk. (Note that for Citi, the Travel desk is actually Connexions Loyalty.) But then that person had to transfer me to someone else, described both as an "expert" and a "specialist." By the time I spoke with the person I needed to speak with, it was about 12:45am. That's right: Even with Citi's flagship premium card, it still took an hour and 15 minutes just to get on the phone with the right person. The agent correctly informed me that she wasn't sure she could do much, given that it was 45 minutes beyond the cancellation window. But she also said something curious: She said that she couldn't have done anything with the reservation anyway, since American "took control" of it, and it was now under American's "control."

Ultimately, I called American Airlines and had the ticket canceled. It took a lot of time on hold, but after multiple calls during which agents would call the Rates desk, I learned that my canceled ticket, which came up as a "bulk" fare (all of the tickets booked with Citi ThankYou points do), would be worth $405, but in the future could only be used toward another bulk fare ticket to American's Asia Region 2.

Booking, Take 2: October 2017

In October, I saw a TPG post about cheap fares to Asia; these have become increasingly common, and they're a great opportunity for mileage runs, especially if you can use special fares earnings like American's to your advantage. I started looking for another flight to HKG. I ended up booking a round-trip flight on American (JFK-LAX-HKG-LAX-JFK) for only $640. I logged in to my Citi account, and booked that itinerary for 51,316 Citi ThankYou points (man, did that devaluation hurt!).

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After waiting about 15 minutes for the reservation to show as ticketed, I called American, and successfully applied two SWUs to my LAX-HKG and HKG-LAX legs. This was a relatively painless process, though the agent had to put me on hold for a while — which now seems par for the course when trying to upgrade flights paid for with points.

Out of curiosity, I started thinking to myself: What would happen if I tried to cancel the ticket? I didn't need to, but I was seriously curious, especially after my experience trying to cancel my itinerary in July. So around 9pm on the same day that I booked my flight and applied the SWUs, I called the Citi Prestige concierge, and braced myself for what I expected to be a long phone call.

After jumping through a few hoops, and waiting on hold for about five minutes, I finally got in touch with the right person at the Travel desk. I was connected to an agent who did not seem to speak English very well, but she tried very hard to be helpful and she understood what I was trying to do. For the avoidance of doubt, I made it very clear to her that I did not want to cancel the reservation. I was just curious as to what she was seeing in front of her, and whether it looked like I could cancel the ticket if I needed to.

She told me that Connexions has a system that communicates with each of the airlines, but this system doesn't seem to provide comprehensive information. On my reservation, she could see the word "Exchanged" — in other words, it looked to her as if I had done something with American to exchange my ticket, but that's all the info she had. And because the reservation was marked as "Exchanged," Citi could not touch it, at all. Even though I was asking about canceling well before 11:59pm the day after booking, the fact that the reservation was marked as "Exchanged" meant that no changes could be made. The agent acknowledged that we were within the allowable time window for canceling, but she could not touch the ticket. I was told that I'd have to contact American if I wanted to make any changes.


First, it seems pretty clear to me (though we can't definitively say, since the Connexions Loyalty agent had no additional info) that the mere clearing of an SWU on American caused my reservation to be tagged "Exchanged" in Citi's and/or Connexions' systems. This fact alone rendered the ticket non-changeable and non-refundable, even when still within the normal window for changes or cancellations. Even worse, neither party really seems to know how this works: Call Citi, and they'll say you have to talk to American to change it. Call American, and they'll say it still shows up as a bulk fare and that you'll have to talk to someone at the point of purchase.

Second, there is the significant likelihood that the exact same thing could happen with other American upgrade instruments, such as using miles with a cash copay. After all, they use the same fare bucket for upgrades that SWUs use, and an American agent would be clearing an upgrade, getting a seat assignment, and so forth.

Third, this raises the possibility that all this could happen with flights booked using other points currencies, such as Chase Ultimate Rewards or American Express Membership Rewards points. If you've had issues changing or canceling a ticket through either of these programs, be sure to let us know in the comments below.

Featured image by Getty Images

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