Some of our biggest points and miles mistakes

At TPG, we’re big fans of maximizing our points and miles to save money while traveling.

Although we have years of collective experience, even points and miles pros (including some of TPG’s very own) make redemption, transfer and earning mistakes.

Here are nine real-world points and miles “oopsies” we have made, so you don’t have to.

A points transfer miscalculation

The biggest mistake I’ve made so far in my points and miles journey was transferring too many points from American Express Membership Rewards to Flying Blue to cover flights for a trip I was planning. This was early on, but I just picked a number that I knew would be more than enough to cover the flights.

I ended up with tens of thousands of points more than I needed for the flights, and I didn’t have a good use for them. They would have been much more valuable to me in their original form of Membership Rewards points. It took me more than a year to find a flight where I could redeem the leftover Flying Blue points.

I should have instead found the exact flight I wanted to take and calculated the exact number of points I needed to transfer to cover those flights. Transferable points are much more useful when you can actually transfer them rather than leaving them in an account where there are fewer options to utilize them.

— Tarah Chieffi, senior writer

A unicorn booking gone wrong

My first big points redemption didn’t work out as planned. In early 2023, I reported on a timely World of Hyatt deal for readers, where stays at the Andaz Maui at Wailea Resort were available for 35,000 to 40,000 points per night on a widespread number of dates. This was a fabulous deal for a Category 8 Hyatt and a chance to save money on my first trip to Hawaii.

Related: A review of The Andaz Maui at Wailea Resort in Hawaii

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Because I didn’t have enough World of Hyatt points at the time, I transferred Chase Ultimate Rewards points through the Chase Travel℠ portal to my World of Hyatt account at a 1:1 ratio. This is one of my favorite transfer partners of the Chase Sapphire Preferred® Card.

I had been waiting for an opportunity like this to transfer the welcome bonus I earned upon opening the Chase Sapphire Preferred.

By the time our reservation for October 2023 came around, we were concerned about the appropriateness of traveling to Maui after the island suffered devastating wildfires in August. We ultimately decided not to go and thus canceled our trip. Luckily, Hyatt credited the points back to my World of Hyatt account, where they remain today. Once you transfer points from your Chase Ultimate Rewards account, you can’t transfer them back to your Chase account.

So, in this case, all was not lost since the points are still available for use. However, they are limited to booking a World of Hyatt property.

— Caroline Tanner, reporter

Being late to the points party

My biggest blunders are not embracing points-earning credit cards sooner and restricting myself to one loyalty program for far too long.

When I first got into the points and miles game, I was slightly hesitant to get a points-earning credit card. Subsequently, I wasted an incredible amount of time trying to earn points using only shopping portals, which eventually led to getting a now-defunct Avios-earning debit card. The earning rate was pitiful, and because it was a pay-as-you-go-style debit card, I also needed to top it up regularly. After some time, I upgraded to an Avios-earning credit card available in the United Kingdom. I regularly look back and regret how many points I missed using this strategy — especially considering I could have probably earned triple the amount I did without additional money.

Related: Why I’m changing my points and miles strategy

More recently, I realized that I had inadvertently chained myself to Avios as my loyalty currency of choice; while I built up a decent haul of Avios, I was restricted to British Airways and its Oneworld partners for my redemptions. Craving the most flexibility and better redemption options, I opened an American Express® Gold Card. This now allows me to earn more valuable Membership Rewards points that can be transferred to various airlines and hotels. I have never looked back and wish I’d seen the light much sooner.

— Jordan Waller, managing editor

Missing out on a sign-up bonus

Instead of earning a 60,000-mile sign-up bonus to book a one-way business-class deal on a Japan Airlines flight to Tokyo, I earned a big fat zero. It was a total rookie mistake. Right after I started at TPG, I decided to sign up for the Citi® / AAdvantage Business™ World Elite Mastercard® (see rates and fees) — Citi’s business card for American Airlines loyalists.

Right now, the sign-up bonus is 75,000 American Airlines miles (after spending $5,000 within the first half five months of account opening), but at the time, the sign-up bonus was just 60,000 miles. Still, the card had a very reasonable spending requirement of just a couple thousand dollars. Unfortunately, I wasn’t paying close enough attention and spent just less than the required amount. I think I miscalculated by something like $12. I called the customer service line, but they wouldn’t budge — no sign-up bonus for me.

Learn from my mistake and make sure you spend the full minimum amount for the bonus. Also, note that the annual fee payment doesn’t usually count toward the minimum spending.

For more details on the current offer, check out our full review of the Citi AAdvantage Business World Elite Mastercard.

— Clint Henderson, managing editor

Did not confirm an offer was still available

I was really stepping up my points and miles game when my wife and I got engaged in October 2020. So, of course, I wanted to capitalize on the massive expense that would be our wedding.

I talked my wife into having our reception at our local Hyatt Regency for a few reasons. First, I’d earn World of Hyatt points through the loyalty program and by paying with my World of Hyatt Credit Card. Also, this location’s wedding brochure mentioned the ability to earn an additional 20,000 to 40,000 bonus points, depending on the amount of money spent on the event. Knowing our budget could earn us enough points to cover at least half of our honeymoon stays, this was a no-brainer.

We began preliminary planning with the Hyatt Regency Rochester’s events staff in early 2021, but with the coronavirus pandemic in full swing, we decided to hold off a bit and set the date for May 2022. About 10 months later, we resumed our planning with the Hyatt staff and finalized all of the paperwork.

Here’s my big blunder: I never actually brought up the bonus points offer in any of our discussions with the Hyatt team. Anyone who’s been through the process of planning a wedding knows how much time and thought goes into these discussions with the venue — from sampling food to programming the event, even down to how they fold the dang napkins. And at no point in thinking through all of that minutia did it occur to me to confirm that we’d be earning those bonus points or check that it was written into the contract.

Well, in the time between when we first talked to the Hyatt team and when we signed the contract 10 months later, the hotel stopped offering that bonus. It was removed from the brochure, and it never actually became part of our wedding package.

I was furious when I eventually realized this, and I spent a good chunk of my honeymoon making bitter phone calls to both the company and the Hyatt Regency Rochester’s events staff. But, really, the onus was on me to make sure that was part of the deal before signing anything. Live and learn. And hey, they still hosted a pretty swell event for us.

— Colin Hogan, newsletter editor

However, the countdown clock on the Avios in my account had started, and Iberia has a rule that Avios will expire after 36 months of no activity. That normally isn’t an issue for me, but it turned out to be an issue for my Avios in the heart of the pandemic.

Many airlines temporarily or permanently relaxed their mileage expiration policies during the pandemic. So, transparently, I wasn’t tracking the date of when these Avios would expire … and so eventually, in August 2022, they did. All 218,013 Avios, worth over $3,000 according to TPG’s December 2024 valuations, were gone.

I reached out to Iberia to plead my case to see if they could be reinstated with a fee or with mercy from the airline, especially given the reality of international travel in those preceding years. Unfortunately, no such mercy was provided.

The Avios were gone for good, and I had to start from scratch, building up enough points to take that big family European trip to Barcelona, Italy and Paris that did eventually happen in the summer of 2024.

— Summer Hull, senior director of content

Honeymoon booking mistake

When searching for award space on United Airlines, I forgot to enter the number of people into my search criteria for a once-in-a-lifetime trip to Madagascar.

I checked for months while researching this trip, and there were plenty of flights on different dates to the country we wanted. However, when we were finally ready to book and conducted a search for two people, there was no availability. (Turns out the partner airline only allowed for one award ticket per flight on certain segments.)

We eventually found a workaround, but it was a big headache that cost us some extra points; it also resulted in us flying in two separate cabins on one leg of our honeymoon. If we hadn’t found a workaround, we would’ve had a bunch of Chase points transferred to United that we couldn’t use.

— Rachel Craft, associate writer

Not maximizing a sign-up bonus

I earned a bunch of Capital One miles from opening the Capital One Venture X Rewards Credit Card the first year it was offered. I was planning a big trip to Israel for my family of four, and I couldn’t decide between using my Capital One miles and my United Airlines miles for the flights. My colleagues advised me to just pay myself back and not convert the miles to another currency. I paid cash for the tickets and then used the miles to pay myself back. (You can cover travel charges by using Capital One miles.)

However, I had to cancel the trip after the Hamas terror attack happened Oct. 7, 2023. So, essentially, all those miles just went to paying my credit card statement. United refunded the money, so I had a huge credit on my statement and negative miles. I had to spend against the miles deficit before I could even start earning again, so I feel like I did not get enough value from my sign-up bonus for that card.

— Erica Silverstein, managing editor

Not counting transferred points correctly

I was an assistant for a “big deal person” and the first time I ever did a redemption was for him, I miscalculated it. I transferred all his American Express Membership Rewards points to Delta Air Lines for two business-class tickets to Paris. However, there weren’t enough points to actually buy the tickets. I was short by just 2,000 SkyMiles, so I called Delta and cried. Because he was a Delta SkyMiles Diamond elite member, they just gave me the difference — something they definitely would not have done if I had been calling for myself.

— Anonymous TPG staffer

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