Manually requesting upgrade refunds from United

Over the Christmas holidays I flew to Palm Springs, California, on United Airlines, which turned into an extremely frustrating experience (but I repeat myself: it was United Airlines). I booked seats in economy, and then a few weeks later saw I could pay for an upgrade request to first class using Mileage Plus miles and a cash copay of $75 per passenger. It was a long flight, I’ve got the Ultimate Rewards points, so I didn’t see why not.

Then, and this is unironically how they get you, I saw I could also pay to upgrade to “Economy Plus” using miles. So I did that too. As you’d expect, the first class upgrade didn’t clear, so we happily took our Economy Plus seats. A few days later both the miles and cash co-pay for the first class upgrade were automatically refunded.

I was happy enough with this process that I did the same thing for our return flight, requesting first class upgrades while paying for confirmed Economy Plus seats. This only required transferring a few additional Ultimate Rewards points since the outbound first class upgrades had already been refunded.

Unfortunately, on the day of our departure from Palm Springs, the United counter had a complete meltdown. We arrived at the airport a couple hours early since we were checking bags, and the United counter — but only the United counter — was in full-blown crisis mode. The proximate cause of this seemed to be that the unmanned baggage kiosks weren’t working and since it’s a family vacation destination almost every passenger had checked bags: golf clubs, strollers, cases of wine, etc. By the time we found the right line, and made it to the front, they weren’t accepting any more checked bags, and rebooked us from our nonstop flight to one connecting hours later to a redeye in Los Angeles.

I then, naturally, paid even more miles to upgrade to premium economy on the new redeye flight, although first class mileage upgrades weren’t available.

To give concrete numbers, at this point I had spent:

• 40,000 miles and $75 (first class upgrade request PSP-IAD)

• 26,300 miles (confirmed Economy Plus PSP-IAD)

• 25,500 (confirmed Economy Plus LAX-IAD)

Since the outbound upgrade request was automatically refunded, I was curious how the two upgrades I paid for on the return flight we got moved from would be treated.

Requesting manual refunds

I kept an eye on my United account, but not seeing any refund activity I went to United’s manual refund request form.

You can plug in your ticket number and last name and see what services United thinks you did and didn’t use. The outbound upgrade request was (correctly) listed as having already been refunded, but the return upgrade request wasn’t available because the return itinerary had been swapped out with the flights we actually took.

View fullsize

Fortunately, right below that are the options to “Add trip” or “Enter receipt details” which allow you to manually add information from trips that don’t automatically populate on the refund form.

When you buy or request an upgrade with Mileage Plus miles or cash, that purchase is issued its own United “reference number” beginning in 016. Each passenger should be assigned their own reference number for each upgrade, and those are the numbers I submitted requesting refunds for each of our Economy Plus seat upgrades and first class upgrades for our original nonstop return flight.

Refunds, fast and slow

I submitted my refund request on the afternoon of January 28, 2026, and the initial refunds rolled in almost immediately with accompanying e-mails:

• January 28: $150 in first class co-pays (posted to credit card Febuary 1)

• January 29: 26,300 in Economy Plus upgrade miles (posted same day)

• February 1: 4,000 in checked baggage miles (posted same day; note I did not request this refund)

On January 31, I received 5 e-mails with identical text referring to 5 of my refund requests:

“Due to the nature of your correspondence, your file has been forwarded to our MileagePlus Department, since it relates to an area of their expertise. Please allow 2 – 4 weeks for your MileagePlus account to be updated. Should you have any further questions regarding this matter, please contact: United Airlines MileagePlus Rewards, PO Box 1394, Houston, TX 77210-1394 or call 1800-421-4655. You may also contact us via https://www.united.com/web/en-US/content/Contact/mileageplus/AccountInfo.aspx.”

Conclusion

It’s unfortunate that United can’t or won’t process refunds automatically in situations where your itinerary changes, but the process of manually requesting refunds is itself extremely quick and easy, so I’d recommend doing it as soon as possible after your travel is completed.

In my case, I’ve been made completely whole for all my unused upgrades, except for the 40,000 miles I redeemed for the leg we were moved from — but the corresponding $150 co-pay has already been refunded to my credit card.

I’m sure in 2-4 weeks I’ll receive a refund of the last 40,000 miles I paid as well, and I’ll post an update then. Obviously I’d rather have the Ultimate Rewards points back than the United miles, but between Lufthansa, Swiss, and Air Canada redemptions, Mileage Plus miles aren’t completely worthless and I’m sure I’ll find a use for them eventually.

Why will there always be another deal?

I like to say that “every deal dies, but there will always be another deal.”

I think most travel hackers of ordinary intelligence understand why every deal dies. If you think of each deal as being designed with some average cost per user in mind, then the two inputs are the expected total cost and the expected total number of users taking advantage of it. If and when a company realizes those expectations were wrong, they look for ways to bring it back into balance, either by reducing the cost per user (devaluations and fee increases) or reducing the number of users (shutdowns and per-user limits).

Obviously this can take a long, long time, either because of incompetent program management, government regulations, or simply low uptake. Even a program that’s hemorrhaging money on a per-user basis can last for a long time if so few people know about it that it takes the company months or years to notice. If a promotion was the brainchild of an ambitious middle manager, they may even realize it’s over-budget but delay admitting they were wrong as long as possible — time that belongs to us.

That crude model (deals die faster the sooner and more expensive they end up being) doesn’t explain the other side of my formula: there will always be another deal. If every deal dies, then one thing you might expect is that the people who kill them will learn from experience and get better and better at developing deals that are more profitable for their companies than they are for us. The people who pitched unprofitable deals will get fired or reassigned (or promoted) to a role where they can do less damage.

But that hasn’t happened. I’m hardly an “old-timer” compared to some folks in the community, but in the 15 years I’ve made it my hobby, for every deal that has died (that I know about — an important caveat in a tight-lipped community) another deal has come up. Sometimes the new deal is less profitable and sometimes it’s more profitable, but it’s always there.

Some people don’t notice this because for a casual travel hacker, especially people who “just have one deal,” the end of their first deal is the end of their travel hacking career. For a lot of people who started around the time I did, that deal was easily-purchased and -liquidated Vanilla Reload cards at bonused merchants like office supply stores and drug stores. For others it was when money orders became too onerous to purchase at Walmart with prepaid debit cards.

I have a family member who earned the Southwest Companion Pass for 3 or 4 years using signup bonuses and manufactured spend. He saved tens of thousands of dollars on Southwest flights, and when he lost access to those deals he said “that’s it for me” and walked away. And good for him!

“When the fun stops,” as the Vegas casino industry slogan says.

It is extremely profitable to borrow, lend, and use money

Travel hacking is a middle-man business. What drives the creation of new deals in the American market is that the “middle” is enormously profitable, so there are plenty of slices of it to cut off.

A popular article circulated back in 2024 laying out one part of that process, specifically about credit card rewards. I don’t know the author and can’t vouch for the specific numbers he uses, but the general idea is obviously correct:

“The heaviest credit card spenders…are wealthy and sophisticated. They use credit cards primarily as payment instruments. Issuers compete aggressively for their business, which is quite lucrative. This is not because they pay much in interest, because while they have higher headline APRs they only rarely revolve balances. It is because ‘clipping the ticket’ via interchange on a high volume of transactions is an excellent business to be in.”

It’s a cliche that "every business has to accept credit cards now,” but that isn’t true. There’s a beloved grocery store in Wisconsin that only accepts debit cards and, for whatever reason, Discover credit cards.

What people really mean is that most businesses choose to accept credit cards in order to stay in business, that is to say, in order to turn a profit, ideally as large a profit as possible. A business that didn’t accept credit cards would have fewer customers, but that would be an obvious tradeoff to make if businesses were consistently losing money on credit card transactions.

The reason businesses accept the interchange fees they’re constantly complaining about is that businesses are very profitable. Credit card processors take a piece of that profit, credit card companies take another, and there is still enough left over for us to take yet another piece of it in the form of third-party and in-store rewards.

As long as business is profitable, there will always be excess inventory

It’s an old cliche that a plane ticket is a product that becomes more and more valuable over time (since last-minute bookers are more and more desperate as seats get scarcer and scarcer) until it expires worthless (when the plane takes off with unsold seats). But while airline tickets, rental cars, and hotel rooms are convenient illustrations, the same process applies to virtually all retail inventory.

The most expensive day to buy new clothes is at the beginning of the season, because that’s when clothing companies know the clothes are most valuable to you. The cheapest day to buy new clothes is during end-of-season sales when stores are trying to unload spoiling merchandise from the previous season.

It’s true in technology, too: Apple charges the most for new smartphones and computers on the day they’re released, and eventually starts giving them away to clear their shelves before the next generation of hardware is released. A two-generation-old iPhone is as worthless a use of shelf space as a two-week-old banana or a flight that departed two weeks ago.

All inventory is constantly spoiling, and all companies are desperate to get rid of it the second it hits their shelves.

What would really stop new deals from arising?

In one sense, these laws are relatively constant under capitalist conditions. Grocery stores in Europe have loyalty programs because their bananas spoil just as quickly as ours do and they too need to get them off the shelves before they expire worthless. That’s what those weekly grocery advertising inserts have always been for. Grocery stores give away turkeys around Thanksgiving because they don’t want to be left with frozen turkeys the day after Thanksgiving, when Americans stop eating them.

Airlines and hotels in Europe are just as eager to get paid something - anything! - for their last-minute vacancies as ours are, so they operate loyalty programs and let people redeem their points for spoiling inventory. Hotel Tonight is still a going concern after all these years.

But the variations you see across borders do illustrate how conditions would need to change to keep new deals from coming up.

• Interchange fees. The fees merchants pay when you swipe rewards-earning credit cards pay for the benefits we receive. But they also pay for the rewards programs we take advantage of being worth operating in the first place. Lower interchange fees would cause credit card companies to reduce points earning as a first-order effect. But they’d also reduce the total number and the price of points credit card companies are willing to buy from their travel partners, and reduce the value of the partnership to those travel partners. American Express is Delta’s biggest customer because they know they can resell the points they buy from Delta to us at a profit thanks to interchange fees. If interchange fees dropped, they’d sell fewer points to us (for example, by changing earning rates) and buy fewer from Delta.

• Profit margins. I have a relative who worked at Best Buy in the early 2000’s, and he used to rave about his employee discount. He bragged about how he could get us 80%, 90%, or 95% off. But that’s not actually how the discount worked. It was what he called a “cost-plus” discount, so he paid 5% over the amount the stuff cost Best Buy wholesale. For screws, cords, wires, all the stuff that littered the aisles of Best Buy back in the 2000’s, it really was a 95% discount because Best Buy didn’t pay anything for that crap. But if you asked him about a new refrigerator, the discount was just 2-3% because the manufacturers of heavy residential appliances drive a harder bargain with Best Buy than the manufacturers of cheap plastic crap do.

Conclusion

The reason I say there will always be another deal is that I don’t see any chance that any of these conditions will go away in the American market any time soon.

Meaningful credit card rewards would go away overnight for most retail customers if the government capped interchange fees, which is why there is a credit card industry lobbying campaign to make sure that doesn’t happen, with the support of consumer-facing ghouls like Gary Leff.

But no part of this system functions without the very high profit margins of the US retail sector. No matter what you’re discounting, there’s no business in any industry that can afford to sell everything it makes for less than it paid for it forever. Fortunately, those very high profit margins are the backbone of the US economy and we have an economy-wide, all-of-government effort to ensure they stay as high as possible as long as possible.

And that is why even when a deal gets so profitable, so popular, so saturated that a higher-up does finally decide to kill it, it has never given me the slightest reason to believe there won’t be another one, because the underlying conditions that gave rise to deals in the first place have not changed.

Interchange fees make generating credit card transactions just as profitable as ever, and profit margins make it as profitable as ever to get people in your store, taking spoiling inventory off your hands.

Getting started with Aligned Incentives, the gift card reseller-cum-bill broker

When I write about gift card reselling, I usually give the rates available on the cards available for sale to CardCash.com. I do not and have never had any financial relationship with CardCash except that they buy my gift cards, let alone an affiliate relationship, but I use them as a reference for two simple reasons.

First, they are still in operation, unlike a lot of gift card resellers that have come and gone over the years.

The Plastic Merchant was one of the more notorious, if not the biggest, gift card reselling collapses because so many online travel hackers were personally affected and wrote about the resulting bloodshed.

Other long-established sites haven’t folded entirely, but have pivoted to other models. Gift Card Granny no longer buys gift cards, and is now just a skinned version of traditional gift card websites. Raise spun their gift card reselling “marketplace” into GCX, which sounds like it is narrowly targeted at people putting extremely high volume through the platform.

The second reason I use CardCash when citing gift card resale prices is that you can check their prices in real time without logging into the website or having an account. This may not sound like much, but I strongly feel that when you write for a public audience then the public should be able to easily check your work, both because it allows errors to be spotted more quickly and because I’m not interested in troubleshooting every reader’s attempts to sign up for every service I mention.

Citing a public website that works on mobile browsers solves both problems, so I cite CardCash.

Getting started with Aligned Incentives

Having said that, a number of readers reached out to encourage me to get up to speed on Aligned Incentives, for a number of very convincing reasons. Most importantly, CardCash doesn’t provide public quotes for Amazon gift cards. Aligned Incentives requires an account, but buys those gift cards at a “base” rate of 91-93.5% of face value (depending on denomination), which makes it one of the most lucrative possible ways to liquidate frequently-bonused “Zift” gift cards at grocery stores.

More about “base” purchase rates in a moment.

Aligned Incentives is open to new users, although they do require you to use Google credentials to set up your account. Their new user guide is also available to the public. It’s not great literature, but I strongly encourage you to read it start-to-finish to understand the kind of company you’ll be dealing with if you decide to proceed.

Notification settings

The very first thing you will notice after creating an account is the sudden onslaught of e-mails. This will become unbearable immediately, so you will start trying to figure out how to turn them off.

Achieve this by clicking on “Notifications” in the bottom left of the main screen:

Then “Opt out of all emails:”

This will shut off the stream of e-mail notifications for the time being.

Next, it’s time to decide what deals you actually are interested in. Expand the “Gift Cards” menu and click “Show Deal Sources,” in purple:

Here you’ll find a list of every merchant Aligned Incentives has ever issued a deal alert for, plus the all-important “Anywhere,” which is how deals are listed when they’re offering to buy gift cards without being attached to any particular deal. After unselecting all (and adding back “Anywhere,”) you should now look over this list to see which merchants apply to you.

I live in a city with both Safeway and Giant grocery stores, but without Kroger or H-E-B stores. Kroger and H-E-B may offer great deals, but I don’t want to get e-mails about them. If you live in Texas your situation might be the exact opposite!

Notifications settings will inform your dashboard

Once you’ve got your notifications set up properly, the third checkbox on the Notifications page starts doing its work: “Check this box to auto-hide deals from your dashboard that do not meet your notification requirements.” With this box checked, after a week or two (when older deals have had a chance to fall off) your “Seller Dashboard” should more or less reflect the deals that are relevant to you.

Selling gift cards

At this point, Aligned Incentives mostly works like a normal gift card reselling site, with a few nuances. First, before you submit gift cards for sale you have to “reserve” specific numbers of cards in specific denominations.

The price and volume for different denominations will be different, but fortunately most merchant gift cards don’t have purchase fees so you should be able to purchase cards in the most lucrative denominations — as long as the clerks at your local stores are willing to go along, of course.

Second, when you’re ready to submit your gift card numbers, Aligned Incentives also requires you to upload a receipt showing you purchased the cards with a credit card. This was a major source of confusion for me at first, but as I understand it they are only trying to ensure that people aren’t laundering money by purchasing gift cards with cash. They’re not verifying the actual credentials of the card you purchased.

Upon even a moment’s reflection this seems absurd: a mobster could simply give someone with a credit card the cash they wanted to launder, and the cardholder could give the gift card and the credit card receipt to the mobster. But criminals are as lazy as everybody else, so maybe adding the trivial friction of the extra step keeps the very laziest of them off the streets.

Payout timing and Aligned Incentives’ shadow banking function

The timing of gift card reselling payouts is the essence of the business: the longer the payout timeline, the longer your money is exposed to the risk of default (as illustrated most pitifully in the case of The Plastic Merchant mentioned above).

CardCash approves my submissions within one or two business days and I receive my payments within a business day or two after that, which gives a payment timeline of between 3 and 6 calendar days: a card submitted on Friday before a long weekend might not be approved until the following Tuesday, with the payment ultimately received on Wednesday or Thursday, but a submission on a working Monday is almost certainly going to be paid out by Thursday or Friday at the latest.

Aligned Incentives has a “standard” payout timeline of 2 calendar weeks from the time your gift card is submitted. Adding a business day for the ACH payment to be received, and the possibility of intervening weekends and Monday holidays, this gives a payment timeline of 15-18 calendar days.

But here Aligned Incentives introduces a secret second function: that of bill broker. This is an industry now associated (if it’s associated at all) with the history of London’s Lombard Street due to Walter Bagehot’s brilliant essay on the industry, but continues after various transfigurations to this day. A common example is freelance and platform workers, who are often offered versions of a deal where their employer offers to pay 100% of their agreed earnings in 6, 8, or 12 weeks or 95% of their pay today.

As exploitative as these employment arrangements are, they only magnify the basic logic that when you are only paid once or twice a month, you are lending your labor to your employer interest-free on the faith that they’ll have the money to pay you when your bill comes due. The sooner you’re paid, the less faith you need to place in your employer: day laborers need only a day’s worth of faith that the money will be there, and the next day are free to place their faith in another employer, perhaps with a better reputation for on-time payment.

It is generally illegal in the United States for non-banking institutions to take interest-bearing deposits. But Aligned Incentives developed a clever workaround: instead of accepting deposits and paying interest on them, they “purchase” merchandise (your gift cards) and pay higher rates for delayed payments. This is the essence of bill brokering, or what is now called “factoring” and in one of its even more esoteric forms “reverse factoring.”

Gift card sales are deposits into Aligned Incentives high-interest-rate ecosystem

What Aligned Incentives really offers is unsecured deposits into its high-interest-rate bill brokerage ecosystem. Allow me to illustrate this with a current deal.

Mid-Atlantic Giant/Stop&Shop/Martin’s grocery stores are currently awarding 8 points per dollar spent on Zift gift cards (worth 8% in grocery rewards or 8 cents per gallon at participating partner gas stations). Several Zift versions offer Amazon.com gift cards as one of many possible redemptions.

If you purchase a $250 Zift gift card, using a credit card that offers 3% in rewards, the purchase itself will generate a minimum of $27.50 in total rewards, meaning what an investor would call their “cost basis,” the amount they’re actually out-of-pocket, is down to $222.50. After converting it into an Amazon gift card, it’s worth $232.50 to Aligned Incentives in 15-18 calendar days, and you can profit $10 for your trouble.

But here Aligned Incentives offers the same deal it would otherwise be illegal for an unregulated financial institution to offer: consider your payment, which you’re entitled to in 15-18 days, as a deposit, and they’ll pay you up to 3% more if you’re willing to wait up to an additional 16 weeks (127-130 days total):

Here the same $250 Amazon gift card, purchased for the same $222.50 after rewards, is worth $239.47, a 3% cash return for leaving your $232.50 on deposit with Aligned Incentives for an additional 16 weeks.

The advantages of an an almost completely flat yield curve

I want to make one final point before concluding. A yield “curve” gets its name from the observation that most investors demand a higher interest rate on longer-term debt obligations than shorter-term ones, both because over longer periods repayment becomes more doubtful and because locking in a long-term interest rate means you’re not able to invest the same money if rates should rise before your first investment matures.

But Aligned Incentives doesn’t use that model. The interest rate they pay on delayed payments is essentially flat across the entire repayment structure:

I only say “essentially” flat because the first two (interest-free) weeks are more significant to the interest calculation the shorter the total repayment period is. The proof of this is left as an exercise for the reader.

Conclusion

To come full circle, I do not believe Aligned Incentives is an especially well-capitalized debtor that is especially likely to full its debt obligations, any more than I thought The Plastic Merchant was an especially well-run organization before they defaulted on theirs.

What I do believe is that if you are already floating debt to Aligned Incentives for payment in two weeks, you’re already taking a credit risk on their ability to fulfill their obligation. If you understand that, then you are ready to decide whether you’re willing to float the same debt for 2-16 weeks longer, with the opportunity of earning elevated returns while your money is on deposit.

“Platform risk” is the most important risk any travel hacker takes, and you should not delude yourself that gift card reselling is any exception. If Aligned Incentives goes under there’s no chance you’ll ever receive your payments, whether you made your deposit one or 126 days ago.

But if you’re willing to risk money on deposit to the platform, then they currently offer a generous annualized rate of return on those same deposits.

Managing legacy and devalued Ultimate Rewards points balances

On October 26, 2025, Chase devalued their Ultimate Rewards program by eliminating the fixed-redemption option of 1.25 cents per point when redeeming newly-earned points held in accounts linked to premium credit cards through their travel portal.

They did grandfather in points earned prior to the devaluation (including pending points), which are now tracked separately in the the Ultimate Rewards portal.

You can view your remaining legacy point total by clicking through to the Ultimate Rewards portal and clicking on the banner reading “There’s been an update to your point value when used for Chase Travel. See what's changed.”

If you have a lot of Ultimate Rewards-earning credit cards, then until you run out of pre-October 26 points, it’s worth thinking carefully about how you manage your point balances.

Premium Ultimate Rewards balances are now stacked: first-in-first-out

The most important thing to know about the devaluation is that all Ultimate Rewards transactions in each account are now paid out of your most valuable points first, regardless of how they are used: for Chase Travel redemptions, partner transfers, or combine points transactions.

Consider an account with 100,000 points earned prior to October 26 and 100,000 points earned after October 26. If you make a 100,000-point Chase Travel redemption followed by a 100,000 partner transfer, the points are worth $250 or $500 more than if you make the transfer first, followed by the Chase Travel redemption, because the first 100,000 points you redeem will always be your more valuable, legacy Ultimate Rewards points.

If you only have one premium Ultimate Rewards-earning card, then that’s all you need to know. But if you have multiple cards, even across multiple family members, as countless readers do, then you have more options.

Transfer newly-earned points to their own account

The simplest workaround is to keep newly-earned points in a different account from your remaining legacy points. For example, I have an Ink Plus account with my remaining legacy points, and an Ink Preferred account I can use to receive newly-earned points. Both allow partner transfers, but partner transfers from the first account would come out of my legacy points first. To the extent possible, I’ll transfer points from my Ink Preferred account before dipping into those legacy points.

Refundable Chase Travel reservations

Another possible option to preserve the value of your legacy points is to make refundable Chase Travel reservations. According to Chase’s FAQ:

“What happens if I cancel a redemption made with points eligible for 1.25x value on Chase Travel?

“Rest assured. If you cancel a redemption made after October 26th, 2025 with eligible points, they will be returned to your eligible points balance. ​However, If you cancel a redemption made prior to October 26th, 2025, the refunded points will not be added to your eligible points balance.”

This makes it sound like if you wanted to use your devalued points for a partner transfer, you could redeem your legacy points for a refundable reservation, make the partner transfer, then cancel the reservation and get your legacy points back.

I have not tried this, and can’t imagine I will have a need to do so, but if you have experimented with this technique please leave a comment and help inform other readers.

Conclusion: not all points are created equal

To a lot of travel hackers, this is all fairly academic: Ultimate Rewards points are so valuable when transferred to their travel partners that 1.25 or 1.5 cents per point is negligible compared to the value they get from Park Hyatt stays and first class flights.

I do some of that goofy stuff, but like most people, most of my travel is still seeing family and friends, and that means not having a lot of control over flight timing and award availability, so I’ve typically redeemed Ultimate Rewards points through Chase Travel once or twice a year, both on cheap flights and when award space hasn’t been available.

That doesn’t mean I’m going to hoard my legacy Ultimate Rewards points: they’re there to be used, and the least valuable point you’ll ever earn is the one you don’t redeem in time. But until the last one’s gone, I’ll certainly be combining points in my non-legacy accounts and transferring from there to partners as a first resort.

My Robinhood shutdown experience: Part 3, resolving my IRA transfer stalemate

I’ve been chronicling my Robinhood shutdown story over the past few months (Part 1, Part 2) as my taxable positions were liquidated and the balance in my taxable account was “refunded” to the various debit cards I’d used to liquidate my manufactured spend and manufacture debit card transactions on my high-interest checking accounts.

Where the story left off, I was deciding what to do with my traditional and Roth IRA balances: Robinhood charges a $100 outbound ACATS fee for in-kind transfers, so I planned to execute a “60-day rollover” of my balances to my external IRA’s.

The problem: a local tax withholding glitch

As they are required to by federal law, Robinhood gives you the option to withhold taxes from IRA distributions, with a default setting of 10%. They also give you the option to adjust that setting for federal taxes. This is important because, to execute a penalty-free 60-day IRA rollover, the entire amount of your withdrawal has to be rolled over. If you don’t notice the 10% withholding, then you have to find the cash elsewhere to “top up” your withdrawal until the withheld money is refunded if and when you file your taxes.

What I found was that when withdrawing my entire IRA balance, I was unable to adjust my local, DC income tax withholding. That would have amounted to a roughly $800 interest-free loan to the government of DC, since I’d get it back when my tax return is processed next year.

Crisis: ACATS doesn’t work

Having given up on the straightforward route, I submitted a transfer request through Merrill Edge to move my IRA balances to my existing IRA there and a new Roth IRA (prepared to pay Robinhood’s $100 ACATS fee).

Each time, the request was rejected, and each time, I escalated my complaint higher, but the only thing Merrill could tell me was that Robinhood was rejecting the transfer because my account was “frozen.”

Since it’s impossible to communicate with Robinhood employees once your account has been shut down, I found that it was necessary to get creative.

Resolution: partial IRA withdrawal

You may recall that I wasn’t able to adjust my DC income tax withholding when withdrawing my entire traditional and Roth IRA balances.

In a fit of inspired pique, it occured to me to see whether I could withdraw less than my entire balance. And, to my very pleasant surprise, the withdrawal of all but a few cents in each account sailed through without even prompting me for withholding information.

The total amount deposited was, however, reduced by the amount of my 3% Robinhood Gold IRA “match.” I wasn’t sure how they would handle this in advance, but I believe they only took out the nominal amount of the IRA match, not any gains I made on the match.

Unresolved: tax treatment

People in the travel hacking community do a lot of shenanigans that generate a lot of tax documents, some of which are useful, and some of which are not useful. As a consequence, there is a very pervasive belief, very much including people who should know better, that tax documents generate tax liability.

This is not true. Underlying activity, whether or not it is reported on documents filed with the IRS, is what generates tax liability. In my case, I fulfilled all the requirements of a 60-day rollover (it was, in fact, a 2-day rollover), but I’m perfectly certain that Robinhood and Merrill Edge will both report me making the same contribution to two different IRA’s. And if the IRS had any enforcement staff left, they might give me a call or send me a letter telling me I’d exceeded my annual contribution limits or owe penalties on my early distribution, or both.

But this is the important thing: I haven’t, and I don’t. Tax paperwork is designed, in the best case scenario, to help you fulfill your tax obligations. But tax paperwork doesn’t create tax obligations. Only the underlying economic activity does, whether it generates tax paperwork or not.

My experience requesting missing Just4U points

The Albertsons/Safeway Just4U program has, for whatever reason, chosen to print rewards so aggressively that it’s oddly become of my main sources of value over the last few years. That being said: not everything always goes right.

Two weekends ago I doubled up the Adidas gift card 10 point per dollar promotion (sellable for 77.5% on CardCash) with the usual 4 bonus point promotion on Saturdays and Sundays, but only received 2,000 Just4U points. As a reminder, these promotions are only partially stackable. Each is calculated as a separate addition to the base earning rate on these cards, so a $500 gift card purchase earns a total of just 6,000, not 7,000, Just4U points: 2 points per dollar as a base rate, 8 additional points per dollar on the weekly promotion, and 2 additional points per dollar on the weekend.

With that in mind, I was still 4,000 points short.

Requesting missing Just4U points

Requesting the missing points ended up being easy, but not obvious. The channel is not through the Just4U part of the Safeway website at all (where you see your deals, rewards, and transaction history), but through the generic “Contact Us” page. Once there, I filled out a brief form using the “Submit Request” button.

I wrote: “I was only credited with 2000 instead of 6000 just4u points for purchasing a $500 adidas gift card despite having added both the 10x and 4x promotions to my account prior to purchase. I am requesting the additional 4000 just4u points to be deposited into my account.”

I submitted the form on the morning of September 13, 2025, and received an e-mail just after midnight the next day from “web.comments@safeway.com” asking for:

• “A screenshot of the 10x and 4x point offers that were added to your account

• A copy or photo of your receipt showing the $500 Adidas gift card purchase”

When I woke up in the morning I send the relevant pictures, which was easy since they were still sitting on my desk from the day before.

In the afternoon of September 15, I received an e-mail stating they’d “submitted a request to manually load the remaining” points to my account.

Satisfied, I checked only occasionally over the next few days but the additional 4,000 points were successfully credited sometime between September 16 and 17. In other words, the entire situation was resolved in somewhat less than 120 hours.

One concern relieved

Like most people with multiple Just4U accounts, many of them use iterations of the same e-mail addresses. I was curious, if not worried, that submitting my proof of purchase from a different iteration might foul the lines between my multiple accounts. That did not end up being the case, as the timeline above suggests.

Conclusion

Whenever something goes “a little bit wrong” people who are already inclined to catastrophic thinking are guaranteed to lose their cool. But not every hiccup is catastrophic and not every solution is all that hard.

Robinhood shutdown part 2: involuntary liquidations, refunds, and Robinhood's clawback fantasy

Last month I wrote about my initial experience having my Robinhood account closed: two of my positions were liquidated, and my Robinhood Gold membership was briefly canceled, then restarted, which allowed me to continue to earn interest on my substantial (to me) cash balance. I maintained 7 individual stock positions with open limit sell orders, one of which was executed at the specified limit price after this saga began.

Since then, another stock (WEN) was sold at my limit price, leaving me with 5 remaining open positions.

Having finally received the overwhelming bulk of my money back, here’s the rest of the story.

Involuntary liquidations

On August 27, 2025, I received 10 e-mails, two for each of my remaining positions: one canceling my outstanding limit sell order, and one informing me that a market sell order had been executed. Since I received the first notificationt that my accounts were being closed on July 30, these involuntary liquidations happened exactly 4 weeks to the day after my first notice.

Refunds to originating sources

On August 26, I received an e-mail from Robinhood stating: “At this time, we are actively working with your financial institution(s) to attempt to return the funds that were deposited into your Robinhood account back to their originating source(s). Thank you for your patience.”

I was naturally deeply curious how this process would work, for two reasons.

First, I had been using my Robinhood account for a wide array of hijinx, including meeting monthly debit card transaction requirements and earning rewards on rewards-earning debit cards. It made sense that they could in principle refund these transactions to the funding debit card using the normal Visa and MasterCard “rails.”

But second, I had a substantial amount of accumulated interest and capital gains in my account: how could they “refund” money that didn’t have a deposit source, but rather was generated by the market itself?

All my funding transactions were reversed for the period between May 27 and July 24, 2025 (the last day I transacted before I was shut down). Because these were processed as individual “refunds,” not as normal transfers out, I have not even attempted to match them up with the corresponding deposits in my various accounts, but using my July brokerage statement as a guide, I’ve received my entire account balance, plus at least part of my August interest, back in my assorted accounts.

In other words, if Robinhood did steal any money from me in the course of this process, it’s in the low double digits.

Robinhood’s clawback fantasy

Robinhood, on the other hand, has a different concern: they think I owe them money because my account wasn’t open long enough to “earn out” the rewards I received by transferring money onto the platform.

While they refunded 100% (plus interest and gains) of my funding transactions, my Robinhood account now has a purported “deficit” of a little over $1,800. As far as I can tell, this reflects the amount of various bonuses I received for transferring in cash or assets that required a holding period of 5 years to fully “earn out.”

It gives me nothing but pleasure to think of the time and money Robinhood will waste trying to extract this money from me, which they will never do.

Traditional and Roth IRA accounts

I also have small traditional and Roth IRA accounts with Robinhood, in order to earn the unlimited 3% Robinhood Gold funding bonus, which were not closed or involuntarily liquidated. Instead, I was given 60 days to liquidate and transfer my retirement accounts. Robinhood charges a $100 outbound ACATS (in-kind security transfer) fee, so to avoid that fee I’ll have to transfer the balances to my external checking account and execute what the IRS calls a “60-day rollover” to my other IRA balances.

Conclusion

Robinhood is a gimmick company for a gimmick economy, which makes it perfectly suited for many specific travel hacking needs.

It also belongs to a sector that is still regulated comprehensively enough that there is almost no chance of them taking your money and never giving it back.

However, that doesn’t mean getting your money back, while inevitable, will be fun or easy, which makes the ancient advice as applicable as it ever was: don’t float Robinhood money you can’t stand to be without, because you have no way of knowing when you’re going to get it back.

My Robinhood shutdown experience: Part 1

I’ve written several times about my various experiences using Robinhood, the app-based investing platform. I’ve found it useful over the years primarily for three purposes:

1. Manufacturing debit card transactions in order to trigger rewards on high-interest checking accounts, since Robinhood allows debit card funding transactions as low as $1;

2. storing cash above the limits of my high-interest checking accounts;

3. and manufacturing debit card transactions on rewards-earning debit cards.

On July 30, 2025, Robinhood notified me they were closing my account. Since I imagine this is inevitable for anyone using their account as aggressively as I was, which surely includes some of my readers, I’ll publish periodic updates as the shutdown process continues, and by the time it’s complete you’ll be able to find a complete timeline of the steps involved.

Initial notification of shutdown

I received my initial notification that my account was being closed on July 30, 2025, a little after 6:00 pm Eastern, after the markets had already closed for the day. The e-mail was short and to the point:

“In light of recent unusual activity detected in your account, we’ve made the decision to close your Robinhood account(s). This can happen when the activity violates our Customer Agreement, or when we exercise the right to close your account as disclosed in our terms and conditions.

Here’s what you can expect over the next several days:

• We will begin closing your Robinhood account(s).

• You’ll be removed from features you had access to.

• Any open positions will be liquidated.

• If any of your accounts are in a negative balance, we’ll apply your existing funds on Robinhood to cover the balance. Any remaining funds may be returned based on eligibility.

• You might receive additional communications or information requests from us during this time—please keep a lookout for these.”

Voluntary sale

The next morning, July 31, I sold my shares in GSY, a short-term money market fund I had been using to take advantage of the $1,000 in free margin that comes with Robinhood Gold, since as I mentioned in a previous post, you cannot both hold cash and use margin simultaneously. This order was executed normally and the funds settled as cash in my account as usual.

Involuntary sales

I had two securities that did not have outstanding sell orders: Vanguard’s long-term corporate bond ETF (VCLT) and a tenth of a “B” share of Berkshire Hathaway (BRK.B) that I’d accumulated through referrals over the years.

On the afternoon of August 4, 2025, those shares were all involuntary liquidated to cash.

Remaining securities

Besides those 3 securities, I also held 7 of my “lottery tickets” in my account: securities that I bought deeply discounted, waiting for their prices to recover and make a nice profit.

Whenever I buy one of these stocks, I immediately place a good-till-canceled sell order against it at my desired capital gain (distinguishing here between my dividend income and my capital gain). As of today, August 19, 2025, none of those orders have been canceled or overridden by Robinhood, although one, for Guess? (GES) was executed at my limit price, so for now my guess is that while those GTC orders are in place, Robinhood can’t or won’t liquidate the positions.

Robinhood Gold interest

On July 30, 2025, I also received a couple of e-mails notifying me I was no longer enrolled in Robinhood’s “brokerage sweep” program and that “by opting out, your uninvested brokerage cash is not eligible to earn interest.” If true, this would be a minor inconvenience, since I would prefer the substantial amount of cash now sitting in the account to earn interest instead of not earning interest.

On July 31, 2025, without any intervention from me, I received another e-mail congratulating me on enrolling in the cash sweep program.

Fortunately, it appears the second e-mail overrode the first. Without getting out my financial calculator, the interest on my cash balance appears to still be accruing at the current 4% Robinhood Gold interest rate. Interest is only actually paid into the account at the end of each month, so I won’t know for another week and a half whether this is just a coding error in the app or if the interest will actually be properly credited.

Retirement accounts

I have a small traditional and Roth IRA with Robinhood to take advantage of their 3% match on contributions and inbound transfers. My automated weekly contributions were paused and cannot be resumed, but my positions have not been liquidated, which matters because uninvested cash in retirement accounts with Robinhood don’t earn any interest at all (unlike at real brokerage firms where it is normally swept into a money market fund).

Retirement accounts are governed under even stricter rules than taxable brokerage accounts, so I strongly doubt Robinhood will liquidate those positions involuntarily, but instead eventually allow me to transfer them in kind to the other IRA’s I have scattered around the financial universe.

They have communicated they will let me know when that option is available, but I haven’t heard anything one way or the other from them about what the timeline for that will be or whether it is linked to the eventual closing of my taxable brokerage account.

Unanswered questions

Obviously the highest practical urgency is in the timeline when my money will be returned to me so I can redeploy it to its highest and best use.

A less urgent but more interesting question is how the money will be returned to me. As mentioned above, I had been using debit card funding from a variety of institutions: CommonWealth One Credit Union, Pelican State Credit Union, Andrews Federal Credit Union, and several proprietary rewards-earning debit cards.

The only relevant information Robinhood has communicated to me is that “If eligible, your funds will be returned to the original funding source or a linked bank account. If we’re unable to return funds via bank transfer, a check may be issued.”

From my perspective the ideal situation would be for a check to be issued, followed by the funds being refunded to one of my rewards checking accounts, with the least favorable option being a refund to my rewards-earning debit cards, since a refund would undoubtedly result in the loss of the rewards corresponding to those transactions.

Conclusion

As comprehensive as this Part 1 may seem, there is quite a bit more ground to cover, so keep an eye out for future entries as I move through the body of the Robinhood shutdown anaconda.

Next time I’ll hopefully provide an account of my contact with financial regulators so far, and future steps I can take as I’m being digested.

My experience paying to liberate US Bank Flexperks credit through American Airlines

Two of my oldest credit cards are my US Bank Flexperks Travel Rewards card and my American Express Hilton Honors Surpass card. My reasons for holding them over the years have changed, as you’d expect given how long I’ve been playing this game.

The Flexperks Travel Rewards used to earn 3 points per dollar spent on Kiva loans (which could be funded with credit cards with no fees), and redeemed for 2 cents each on certain flight redemptions, while the Surpass used to offer bonus points at drug stores, which financed a lot of my hotel stays while I was in grad school.

But the principle reason I’ve kept both cards for all these years is that they offer bonused earning on grocery store purchases. The Flexperks Travel Rewards card earns 2 Flexpoints per dollar (worth 3% in paid flight and hotel redemptions) and the Surpass earns 6 points per dollar, which is worth roughly 3% depending on your own Hilton redemption preferences. Given how valuable grocery store promotions are, I have found it essential to have at least a few credit cards that earn bonus points there.

But this summer I had my first experience converting a Flexperks Travel Rewards redemption into American Airlines travel credit.

The original reservation

My hometown has always been expensive to fly in and out of, so I usually redeeem Alaska Airlines Mileage Plan miles for my flights, since Alaska has last-seat-availability on their own flights and their Portland and Seattle hubs provide an easy one-stop connection.

For a planned trip in June, the mileage redemption was so expensive that I decided to instead use Flexpoints to book paid American Airlines flights, which worked out to 63,781 Flexpoints for two tickets costing a total of $956.72 (including a nuisance $13.98 “Flight Facilitation Fee”).

The cancellation

We ended up not being able to take that trip, which raised the question of how to get value back out of our canceled flights. If I already had future paid travel plans on American Airlines, I believe I could have called US Bank’s travel agency and asked them to use the value of the ticket to book new flights before our original flights departed.

But I didn’t have future paid American Airlines travel plans, and since the flights I booked were changeable, but not refundable, I decided to cancel the flights through American Airlines’s website, instead of through US Bank’s “Travel Center.”

This went smoothly, and I could pull up the cancelled tickets’ value through the American Airlines website. But every time I tried to use the credit, the website prompted me to call in.

The rebooking

A few months later, I identified a perfect use for that American Airlines flight credit: while outbound flights for Thanksgiving weekend were available with Alaska miles as usual, cash return flights cost almost exactly as much as a roundtrip would: $1071.94, or about a hundred dollars more than the American Airlines credit I held in this unfortunate liminal state.

Figuring I would get a blog post out of it either way, I first called US Bank to see if they would allow me to use my “Travel Center” reference number to rebook my flights. They would not, but they did tell me to call American Airlines at their generic customer service number 800-433-7300 to use the credit with them.

After a few tries navigating their phone menu from hell, I struck on a different idea: American Airlines still allows you to prepare reservations online and then “hold” them to pay over the phone or in person.

The liberation fee

This gambit ultimately worked: once I had the reservation on hold, I could use the phone menu to skip directly to a representative who was able to pull up my held reservation. and I then asked him to apply my travel credits.

I was expecting to pay the fare difference between my flights, but the representative quoted me a price (after applying the credit) $100 higher. When I pointed out the discrepancy, he explained that they charged a $50 per-ticket fee for tickets booked through third parties.

Why it matters

Most paid domestic airline tickets are now “flexible” in a way that was rare before the COVID-19 pandemic, and the price difference between inflexible (“non-changeable,” “non-refundable”) and flexible fares is as low as it has ever been in my adult life.

But if you book paid fares through travel portals using fixed-value points like US Bank Flexpoints, Chase Ultimate Rewards, or American Express Membership Rewards, you should be asking how and whether you, personally, get to take advantage of that flexibility.

Many years ago I wrote about how US Bank was able to successfully and automatically convert a refund I had individually negotiated with Delta Airlines into redeposited Flexpoints. Knowing that the value of your redemptions can be reclaimed is one way you can be assured you’ll get something close to the prospective value you assign them while you earn them. If a sudden change in plans really could wipe out $1,000 in travel value, then you’d be insane to continue earning points in that program.

I found the $50 fee American charged me to “liberate” the value of my tickets as annoying as any sensible person would, but I found it a lot less annoying than being ask to forfeit the entire value of my US Bank redemption, and it has strengthened my fondness for the Flexperks Travel Rewards program in general.

An excellent Just4U offer on Zillions gift cards

I’ve written several times about “Zillions”-branded gift cards, and the three broad buckets I place them into: fixed-value, loose-variable, and tight-variable. All three can be exchanged for store-specific gift cards, which can then be used or sold. While not of much interest in their own right, these cards become extremely interesting when they earn bonus points in the Just4U loyalty program shared by Safeway, Albertsons, and dozens of other sub-brands across the country, as they are through Saturday, June 28, 2025.

The deal

Zillions cards currently earn 10 Just4U points per dollar spent. These cards have no activation fees, and can be purchased with credit cards wherever employees allow it.

Most weekends, Just4U runs a stackable promotion where gift card purchases earn 2 additional bonus points per dollar (this is confusingly branded as “4 points per dollar” since gift cards earn 2 points most of the time). If that promotion runs again this Saturday, then Zillions cards should earn a total of 12 Just4U points per dollar.

I value Just4U points at roughly 1.85 cents each, so on Saturday this deal will generate a rebate of about 22.5 cents per dollar spent, plus however much you earn with your credit card on grocery store spend. If you redeem your Just4U points for the most valuable grocery redemption, you’ll receive $20 off for 1,200 points, or 1.67 cents per point.

Of course, what you’re spending the money on is a Zillions gift card, so the question is how to get your money back out of the system. As a reminder, fixed-value Zillions cards cost $100 but allow you to redeem $105 for store gift cards. The best resale rate I was able to find on CardCash was 80% on Saks OFF 5th, or $84 per fixed-value Zillions card.

The most valuable Just4U redemptions have a capped number of redemptions each week, but if you sign up for the Freshpass program, which costs $99 per year or $49 if you qualify for SNAP, then your points don’t expire, so you can redeem them for their highest value week after week.

Conclusion

This is both an outstanding deal in its own right, one I myself am planning on hitting moderately hard this Saturday, and a nice reminder that travel hacking is in so many ways a subset of extreme couponing. Stocking up on toilet paper may be less glamorous than first class flights around the world, but the principle is identical and more often than not, so are the means: pay as little as possible for the things you want or need.