Upgrading a two-hour flight — reader mistake story

Dec 9, 2019

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Today, I want to share a story from TPG reader Evan, who only got part of the upgrade he was hoping for on a trip to Hawaii:

I was planning a trip to Honolulu, and was about 100 miles shy of earning United Premier Gold status, so I decided to book a one-way United flight from Seattle to Honolulu with a short layover in San Francisco. About two weeks before my flight, I decided to look into upgrading with miles to business class. There weren’t any seats available, so waitlisting was the only option. The price was steep at 27,000 miles, but I read that the miles would be refunded back to my account if a seat didn’t open up. Since the flight was just two weeks away, I figured the upgrade probably wouldn’t come through and I would just get the miles back.

One week before the flight, I was upgraded to business class on the short SEA-SFO flight. This wasn’t ideal since I really wanted it for the longer flight. The day of the flight came and I didn’t get the upgrade on the SFO-HNL segment. About a week after, I called United to explain my situation, and that the miles for the upgrade on the second segment hadn’t been returned to my account. I was assured they would be, and was asked to call back if I hadn’t been refunded in a few days. I waited another week and called back, but this time the agent said that since one of the flights on my domestic itinerary was upgraded, the upgrade was considered successful and no miles would be returned.

I explained what I had been told previously, but the agent and her supervisor just said that, unfortunately, that is their policy, and I could send a message via their online form. Apparently, I didn’t read the details of upgrade awards well enough, so I spent 27,000 miles on a two-hour domestic business-class seat. If I had read the policy thoroughly, I would not have tried to upgrade my seats. I hope my 27,000-mile mistake helps someone.

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The terms and conditions for MileagePlus Upgrade Awards specify that an upgrade is considered successful if any segment of your travel is upgraded (with a few exceptions surrounding Polaris business class). That means when you use miles to upgrade an itinerary with multiple segments, you run the risk of only being upgraded on a short segment like Evan was. He effectively paid 27,000 miles on top of his fare to sit up front on the two-hour flight from Seattle to San Francisco — a terrible deal considering first-class saver awards on that route go for 25,000 miles outright.

To avoid such outcomes on trips that include a stop, try upgrading individual segments rather than your whole itinerary. You’ll first have to decide which segment to prioritize — the longer SFO-HNL segment is the obvious choice in Evan’s case, but the decision may be less clear depending on your routing and potential cabin configurations. You’ll then have to speak to a MileagePlus agent by phone, as requests to upgrade part of a multi-segment itinerary can’t be processed online. If your upgrade request clears, you can call back and try to extend it to the rest of your itinerary. There’s some chance you’ll be upgraded only on the preferred segment if there’s no space on the others, but that beats getting upgraded only on the less desirable segments for the same price.

Related: Your ultimate guide to upgrading with miles

I appreciate this story, and I hope it can help other readers avoid making the same mistake. In appreciation for sharing this experience (and for allowing us to post it online), I’m sending Evan a gift card to enjoy on future travels, and I’d like to do the same for you. Please email your own travel mistake stories to info@thepointsguy.com, and put “Reader Mistake Story” in the subject line. Tell us how things went wrong, and (where applicable) how you made them right. Offer any wisdom you gained from the experience, and explain what the rest of us can do to avoid the same pitfalls.

Feel free to also submit your best travel success stories. If your story is published in either case, I’ll send you a gift to jump-start your next adventure. Due to the volume of submissions, we can’t respond to each story individually, but we’ll be in touch if yours is selected. I look forward to hearing from you, and until then, I wish you a safe and mistake-free journey!

Featured photo by Ian.CuiYi/Getty Images.

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