The Upgraded Points Team’s 2025 Party Fouls

What was your biggest blunder this year in the world of travel and/or points? Did you miss a flight? Forget to cancel a hotel room and have to pay for it, even though you didn’t sleep there?

Maybe you missed a credit card bonus or paid for a purchase with the wrong card, like members of our team did. But did you accidentally cross into another country with an expired passport?

Here are the worst blunders the Upgraded Points team made in 2025.

Michael Y. Park, Senior Editor

If Upgraded Points is handing a crown for biggest travel party foul of the year, you might as well go ahead and start calling me “Your Majesty” right now.

I’d gotten to do a lot of fun and interesting things in 2025 — like exploring Portland, Oregon, for the first time, sleeping in a haunted hotel, cycling around Nantucket, and gorging myself at Epic Universe — but the one thing I somehow hadn’t managed to fit in was any international travel. So for a last hurrah before the year ended, my family and I drove up to Montreal, Quebec, before the new year to eat smoked meat, stock up on St-Viateur bagels, and take care of some business I had up there.

It was an easy trip: We got up early with a full tank, drove straight there except for a short stop along the way for Stewart’s peppermint ice cream, and found only 3 cars in front of us at the border. The Canadian immigration officer checked our passports, asked us the standard questions (“Where do you live?” “Why are you visiting?” “Do you have anything dangerous or agricultural with you?” “Where are you staying?”), and then wished us happy holidays and a pleasant visit.

Fine and dandy, right?

Not so fast. While taking care of that business I had in Centre-ville, I had to pull out my passport again. When the guy helping me took a look, he paused, checked it again closely, then asked, “I’m sorry, where’s the expiration date on American passports?”

We told him where to find it, on the first real page toward the bottom, same as on Canadian passports.

He looked again, grimaced, rotated my passport and slid it back to me, pointing to the expiration date: June 2025. I’d gone half the year having completely brain-farted on renewing my passport. Worse, I’d traveled deep into a foreign country with an invalid passport.

Luckily, I have an enhanced driver’s license (not expired), which allows me to travel between the U.S. and Canada by land or sea (but not by air), and we drove back to the U.S. and across the border without issue. And, of course, I started the passport renewal process immediately upon my return. But as far my travel party fouls go — and I’ve had plenty of truly bad ones — almost getting stuck in a foreign country with a bad passport has already made it into my record book.

Keri Stooksbury, Editor-in-Chief

My first party foul happened just as the clock struck midnight from 2024 to 2025. I was at the tail-end of Bilt Rewards’ instant Hilton Honors status promotion (which has since lapsed). This promotion offered Hilton Honors Gold status through 2026, provided 8 nights were completed by December 31, 2024. Even though I enrolled in the promotion in October 2024 with no stays in mind, I was glad I did when I later booked an 8-night stay over the Christmas holiday. Unfortunately, I neglected to read the fine print and understand Hilton Honors’ policies. My 8-night stay ended on January 2, 2025, and the entirety of my nights were credited to 2025 instead of 2024 — after the promotion technically ended.

My 2025 is bookended with party fouls, as I just had another. Again, it always pays to read (and reread and reread again) the fine print. I recently applied for a new American Express credit card and received a pop-up notification stating that I wouldn’t be eligible for the offer. I researched a few “how to get out of Amex pop-up jail” options and decided to try again the next day. I moved too quickly on the application by clicking buttons and didn’t take screenshots or a video of my application process to document my actions. As a result, I was still in pop-up jail, but I was approved for the credit card, albeit without the welcome offer … only I didn’t realize this until weeks later. Amex still showed the bonus tracker in my account, so I happily met my minimum spending requirements and then wondered where my bonus was. Instead of the 90,000 miles I was expecting, I only received 6,000 miles for my 1x purchases. I’m bummed that I missed out on the bonus, but lesson learned for 2026!

Tiffany Eastham, Director of Compliance

It wouldn’t be a year of expert travel without a few silly mishaps. My first travel party foul comes from nearly missing those welcome offer bonus points.

I was approved for the Atmos™ Rewards Summit Visa Infinite^® card earlier this year. I planned to add it to my Amazon account to hit that minimum spend, since many of my regular purchases are made through Prime. I don’t know what happened, but after nearly 2 1/2 months of (clearly) being absent-minded about it, I realized that my Atmos Rewards Summit card had never actually been linked, and I’d spent next to nothing on it all this time. What ensued was 2 weeks of panic spending on items I would eventually use — like cat food. The cats were happy, but I was not.

Consider another cautionary tale: If you link a new bank account to your credit card, that action will most likely cancel your autopay settings. When I failed to realize this, I experienced my first ever missed payment, late payment fee, and interest accrual on both my Platinum Card^® from American Express and American Express^® Gold Card accounts. I’m still bitter about that.

And finally, I was generously gifted a World of Hyatt Guest of Honor Award — a benefit that grants you top-tier Globalist perks, such as free breakfast and elite lounge access during your stay. I attached that coveted award to my booking while visiting Krakow, Poland, only to later find out, mid-stay, that this particular hotel offered free breakfast to all guests, and there was no club lounge on the property. A true waste of a benefit that could have potentially saved me hundreds of dollars (and tears) if staying elsewhere.

Ryan Smith, News Managing Editor

What do you know, another story about nearly missing a welcome bonus offer from being absent-minded …

After opening the CitiBusiness^® / AAdvantage^® Platinum Select^® Mastercard^® at the beginning of the year, I put a few purchases on the card and then seemingly forgot about it.

Fast forward to 10 days before the welcome offer deadline. I needed to spend another $3,000 on the card to earn the bonus. The problem? An oddly low spending limit of $2,000 on my new card. I needed to spend $3,000 on a credit card with a $2,000 spending limit — and do so in 10 days.

I paid everything possible on the card until reaching the $2,000 limit, and then I made a payment to bring the balance down to $0. In theory, I’d now be able to spend more on the card to complete the final $1,000 of spending needed for my 75,000-mile welcome bonus.

Not so fast.

Citi put a hold on the payment. I called Citi 5 days later to ask why my card had no available spending balance after making a payment, and we had to 3-way call my bank to confirm that the payment was processing, there were sufficient funds, and then wait another 24 hours before Citi credited the payment to my balance, finally opening up spending ability.

I made my final purchases to achieve the welcome offer in the few days remaining, but I was definitely biting my nails while waiting for the purchases to hit the card, nervous that something would post late and cause me to lose 75,000 AAdvantage miles. It worked, but it was stressful.

Christine Krzyszton, Senior Finance Contributor

My greatest fails of the year were mostly recent. My flight from New York City (JFK) to Detroit (DTW) was delayed, meaning I would miss my onward connection. I booked The Westin Detroit Metropolitan Airport while we were departing from JFK. Miraculously, I made the 20-minute connection, but the Westin would not move the reservation to a different date (I had to at least try) or check me in for the elite night credit. Worse yet, I was listed as a no-show the next day. It was a very expensive mistake.

The other fail was a recent Dell purchase that I inadvertently charged to the wrong The Business Platinum Card^® from American Express. Fortunately, it wasn’t for the full up to $150 Dell credit, and it was an item I could use.

Victoria M. Walker, Senior Content Contributor

My biggest fail of the year was overestimating my nonexistent swimming ability. In August, I flew to Italy to vacation on the Amalfi Coast and spend time sunbathing at a beach club in Positano. I took a paddleboard out into the water, which then flipped, plunging me into the water — and I’m not a strong swimmer. Luckily, 2 kind people pulled me out and carried me back to shore, but it was just the push I needed to sign up for swim lessons finally.

Lori Zaino, Senior Content Contributor

My biggest travel-related fail this year was related to credit card perks. With 11 cards, it was bound to happen — even though I use spreadsheets from the CardPointers app to track my perks. I used my Citi Strata Elite℠ Card to book $300 worth of flights in Citi Travel to get the $300 travel credit, but I screwed up.

I wrongly assumed the credit was similar to the $300 Capital One Travel credit on the Capital One Venture X Rewards Credit Card, which is valid for all Capital One Travel purchases. I thought it would cover any type of travel, but in reality, the $300 credit is only valid for hotel purchases made through Citi Travel. Whoops! At least I got 6x Citi ThankYou Points on the flights for booking them in Citi Travel. And don’t worry, I later used the credit for a hotel in Singapore, so I didn’t fully lose it. Still, for a self-proclaimed credit card expert, this error made me feel pretty silly.

Chris Hassan, Social Media and Brand Manager

I consider myself pretty well-versed when it comes to traveling with kids. We’ve been traveling internationally ever since our daughter was 3 months old. Yet, almost 12 years and 1 more kid later, I can assure you that mistakes can still be made — even by “the pros.”

My family and I live in Brazil, so we are constantly dealing with different rules and regulations when it comes to traveling with minors. In the U.S., IDs are not needed when flying domestically with an adult (odd, but convenient); however, in Brazil, an official ID or birth certificate is required.

In September, my family of 4 was boarding a quick flight from Rio de Janeiro to São Paulo, and my 6-year-old was denied boarding because we had only brought a copy of his birth certificate, not the original. My daughter had an official government ID with her, so she boarded with my wife as they were headed to a Backstreet Boys concert they didn’t want to miss.

Since Tommy and I were just tagging along for the nice hotel, we stepped out of line to figure out a plan.

Unfortunately, the only option (besides bailing on the trip) was to drive back home and grab his passport — a 3-hour round-trip journey in Friday rush-hour traffic. Once we got back to the airport, it took another 2 hours in line to get rebooked, plus a nice $200 rebooking fee to get us on the last flight of the day.

What was supposed to be a quick lunchtime flight turned into an 8-hour ordeal. We made it, though, and enjoyed our stay at the Westin São Paulo while learning a valuable lesson!

Final Thoughts

From paying for a hotel you didn’t stay at to messing up your attempt to use a credit card perk and issues with welcome bonus offers, we had several mess-ups this year. We also had some ID … issues, let’s call them. And the good news is that no one went to jail related to these party fouls, thankfully.