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.

Using Fluz as intended: don't sleep on expiring "boosts"

Over the years I’ve occasionally mentioned on the blog, and described extensively in Subscriber-only Newsletters, Fluz, the third-party gift card merchant. As a reminder, the publicly-available version of the site sells gift cards at hundreds of merchants and offers a rebate in the form of rewards that can be redeemed for additional gift cards or withdrawn as cash, once certain thresholds are met.

A quirk of the site when used as intended are “boosts,” which can be used to receive an increased rebate on a single gift card purchase, typically 25% on the first $10 in value. A few weeks ago heavy users of the site realized they had somehow accumulated dozens of these boosts, which are expiring May 5. I checked and had 20 in my own account.

If you can find boost-eligible gift cards to stores you typically pay cash at, this is a no-brainer. Apple gift cards, for example, can be purchased in $10 denominations and loaded into your Apple account for purchases across the Apple ecosystem. Perhaps needless to say, it is difficult to find 25% discounts on brand new Apple equipment.

Unfortunately many merchants have minimum values above $10, which correspondingly reduces your total savings. Here are a few other obvious options for merchants where you might already be spending cash:

• Grubhub ($10 minimum)

• CVS ($10)

• Ace Hardware ($10)

• Target ($10)

• Starbucks ($10)

• Walmart ($10)

• REI ($10)

• Ebay ($10)

• Uber/Uber Eats ($15)

• Lyft ($25)

• Amazon ($30)

Note that some merchants, like Apple, allow you to load multiple gift cards into a single account balance, while other merchants, like Ebay, save individual gift cards and limit the number that can be used in a single transaction. Before loading up on gift cards to a single merchant, make sure you know which model that merchant uses.

Quick hit: no, Freedom family product changes don't reset your quarterly bonus spend

One of my favorite techniques is requesting product changes from Chase personal credit cards where I received a signup bonus to Freedom cards that earn 5 Ultimate Rewards points per dollar in their quarterly bonus categories, on up to $1,500 in spend per account.

This technique doesn’t get written about as much as it used to because most travel hackers prefer to chase signup bonuses, which quickly puts them over Chase’s rules for approving personal credit cards.

As a reminder, you usually can’t get a Chase signup bonus if you already have a specific card, or have received a signup bonus for it in the last 24 or 48 months, depending on the card. One way to start that clock ticking again is to request a product change to another card. My current preference is for the Freedom Flex card, since it combines the quarterly bonus categories of the Freedom (not available for new signups) and the uncapped 3 Ultimate Rewards points per dollar spent at drugstores of the Freedom Unlimited.

I had done this a number of times in the past, so I was sitting on 3 Freedom cards on which I had already reached the quarterly cap when I applied for and completed the minimum spend requirement on my new Freedom Flex. Once that signup bonus posted, I called in and requested product changes from my Freedom cards to Freedom Flex cards. Note that when doing this a new card and card number will be issued, so be sure to keep an eye on any recurring bills that are charged to your cards.

What I was unsure of was whether these product changes would reset my quarterly bonus earning cap, because I had never changed products within the Freedom quarterly bonus family; I had only moved to and from quarterly bonus cards, not between them. If product changes reset the quarterly bonus counter, then during promising quarters you could max out each card twice, as a kind of backdoor “upgrade bonus.”

But, regrettably, the quarterly bonus counter was not reset by my product change, so even though the Freedom Flex cards have new numbers, it appears everything else about the old Freedoms was saved and ported over to the new accounts.

"How do we scale this?"

One of my favorite questions travel hackers ask is “how do we scale this?” The implicit answer is, usually, “we don’t.” Contrary to what economists pretend to believe, the world is in fact chock-full of arbitrage opportunities. What is true is that most of those opportunities are difficult or impossible to scale.

Here’s my personal breakdown of techniques used to increase scale, and the obstacles to doing so.

Brute force and constant returns to scale

The most obvious scaling strategy is to multiply your own effort. If you have a technique that generates a known amount of value per hour you spend on it, then you can get twice as much value by spending twice as much time, usually up to some limit. In a simple example, if it takes you an hour to manufacture $10,000 in in-person spend at one grocery store, and you have identical access to five grocery stores, then you can spend 5 hours and manufacture $50,000.

Automation and transformations

A lot of high-volume travel hackers focus on automation as a way to scale their techniques, and automation is one of the many tools I put in the broad category of “transformations.” Transformations are when the design of programs can be understood differently by the customer than by the business in order to scale techniques, either to get a higher return from the same amount of time or money, or to reduce the time or money needed to get the maximum return.

To give a classic example from my own practice, for many years the US Bank Flexperks Travel Rewards Visa offered 3 points per dollar spent on charity, worth up to 6% when redeemed through their travel portal. They also coded Kiva, the microlending website, as charity. People were thus able to earn as much as 6% in travel on loans of as little as a few months, and many of us did, transforming a modest discount on charitable giving into an extremely high-yield investment vehicle.

A more contemporary example is the rewards (often branded as “Kasasa”) checking accounts that offer some of the highest-earning, most liquid savings vehicles. They typically require 12-15 debit card transactions along with a direct deposit in order to earn their advertised rates. Meeting these requirements as they intend would seem to require, as they intend, reorienting your entire financial life around doing so. But when you’ve broken down the requirements to their individual parts, you can transform meeting them into a matter of a few minutes per month.

American Express cards have acquired a reputation of being “coupon books,” but a lot of the pain of redeeming those coupons (and getting back the value of your annual fee) can be transformed into painless routines:

• American Express Hilton Honors Surpass cards can be used to buy $50 in physical gift cards on the first day of each quarter to trigger the quarterly statement credit;

• Monthly statement credits for Resy and rideshare services or Shake Shack and Grubhub can be triggered by gift cards or subscription services.

All these are transformations: the company wants them to dominate your thoughts, but a few simple calendar reminders can guarantee you maximize the value of each credit without having to keep track of any of them individually.

Teammates, comparative advantage, and the benefits of trade

I call teammates everyone you partner with in order to take advantage of different circumstances, what economists call your “comparative advantage.” These can take all sorts of forms: some people have access to grocery store manufactured spend while other people have access to gas stations. Some people have more Chase cards than they’ll ever be able to maximize the value of, while others pile into American Express cards and are blocked from signing up for new Chase cards.

A lot of bloggers have a kind of “view from nowhere,” where every person has access to every credit card and each can follow prescribed steps from scratch, but it takes almost no experience to know that’s absurd. Every individual travel hacker’s situation is different, and it takes only a little more experience to identify which parts of the game you’re interested in pursuing most intensively. Finding other people with complementary interests is a way to scale each of your efforts by getting the most value from the parts of the game you’re most interested in.

The most obvious candidates for teammates are family members, precisely because there’s usually not any need to “divide” effort or results at all: everyone gets to go on the family trip, regardless of whether they made a “fair” contribution to paying for it at all. Some bloggers have affected to call these teammates “Player 1,” “Player 2,” and so on.

Employees

One of the most common questions people ask when they find out about the existence of travel hacking is, “that sounds great, but I don’t want to do it, can I just pay you to do it for me?”

There are people and situations that make this possible, but fewer than people wish or expect. The main problem is that almost anything you can train people to do on your behalf, they can do on their own behalf. You are the middle man, and unless you have both knowledge and money that are impossible to steal, your employee will quickly get the drift and go to work for themself.

The Verge had a humorous story about this very phenomenon in my home state of Montana, where resellers would continuously set up drop-shipping warehouses only to find their employees, having mastered the skill of packing and unpacking Amazon shipments after a few months simply set up their own tax-free reselling businesses.

Readers as force-multipliers

Another way to scale a technique is simply to share it. This has all the advantages of the techniques above.

Brute force techniques will have more people applying more brute force and yielding more benefits.

If you know how to transform a technique from difficult to hard, then more people will save more time and effort.

If you know how to trade personal or regional advantages with other people, then telling them how will result in more benefits for everyone in those situations.

And if you tell people how to hire employees to solve their problems, then more people will have their problems solved and more people will be employed.

The problem, of course, is that you don’t get a cut. What’s up to you is how big of a problem that is.

How does Hilton price 5th-night-free awards?

I manufacture a lot of Hilton Honors points with the American Express Surpass co-branded credit card, and I redeem almost as many. The Surpass earns a free night certificate that can be used worldwide after spending $15,000 per year and Diamond status after $40,000 in spend, but I am perfectly happy earning 6 points per dollar spent at grocery stores all year.

I try to redeem points for at least 0.5 cents each, and do not have any difficulty finding opportunities to do so, although as always you have to be careful that you’re comparing redemptions against the money you would spend instead, not the cash value of the room you redeem points for.

For example, I stayed at the Conrad Hilton Midtown last weekend for 95,000 points per night (plus two of those free night certificates), which translates to something like 0.7 cents in value, but of course I wouldn’t spend $675 to spend the night in New York City, so it would be absurd to say I earned 4.2% in value on my grocery store spend.

One way to maximize the value of that spend is by using the fifth-night-free benefit on award stays whenever possible. Fourth- and fifth-night-free offers are pretty common across the industry, and Hilton’s is one of the most straightforward: to trigger the benefit, all you have to do is book a standard room for 5 or more nights entirely with points.

That’s how the benefit is triggered. Understanding how it’s calculated is trickier.

There are lots of ways to calculate the value of a night

I mention that other programs have free-night benefits for stays of a certain length because they illustrate how a simple-sounding benefit can have both opportunities and perils. Most importantly, how does the value of a fifth-night-free benefit change when the nightly rate varies over the course of the stay?

Chase IHG Rewards credit cardholders get a “true” fourth-night-free: the point cost of the specific night which happens to be fourth is zeroed out. This creates opportunities to stage your reservations so that the most expensive nights of your stay are the fourth ones and increasing the potential value of the boost to your points’ value over 33%, and the risk of “wasting” the benefit on a cheap fourth night..

The Citi Prestige card offered what they called a fourth-night-free benefit, but it was calculated as just 25% off the (apparently-inflated) prepaid cash rates offered through their travel portal. This meant the maximum value of the benefit was capped at 33%, with higher portal rates grinding down the value of the benefit from that theoretical cap.

Marriott Rewards’ version stretches the concept to the breaking point: on 5-night stays, the lowest-priced night is deemed to be the “fifth,” so on stays with varying rates you will never capture the full 25% boost boost in value; only on five-night stays where each night is priced equally do you get the maximum value from the benefit.

Hilton seems to use a “trimmed” fifth-night-free calculation

Since I have a fair amount of experience redeeming Hilton points, I’ve had the chance to observe how Hilton handles this inevitable question: how many points should you expect to save when using a fifth-night-free benefit?

First, to trigger the benefit, the same room type has to be available for the entirety of your stay. That means you need to go further than the Hilton award calendar, since you might see lower rates for one-night stay in a room type that isn’t available for all five nights.

Second, if the room type you’re booking has no change in price over your stay, then it’s as irrelevant as you’d expect: you save 20%, getting a 25% boost to the value of your points.

When the points rate varies over the course of your stay, then things get interesting. On the checkout screen, you’ll see a rate listed for each of the first four nights and “5th Night Free” listed next to the last night. But those first four rates are not necessarily the rates you’d pay if you were booking each night individually. Instead, Hilton sometimes “trims” those, slightly increasing or decreasing the price of each night.

Usually, but not always, this is done in Hilton’s favor: the first four nights will cost more as part of a five-night reservation than as four one-night reservations.

At this point, I would like to be able to pull off the napkin and reveal that I’ve reverse-engineered the precise formula Hilton uses to make these trims, but that’s not true. I spent the morning poking around the website and running experiments, and concluded that sometimes Hilton does this, sometimes it doesn’t, and when they do it’s usually against the customer’s interests.

Here’s a screenshot of the basic principle at work:

To walk through what you’re seeing there, a five-night stay starting on May 4 costs 199,000 Honors points, while the same five nights priced individually cost 248,000 points. In this case, the night of the 6th is “trimmed down” to 48,000 points, so the reservation costs 1,000 points less than it would if Hilton offered a true fifth-night-free, like IHG.

Meanwhile, a five-night stay starting on the 5th costs 196,0000 Honors points, while the same five nights would cost 253,000 points on their own. In this case, the nights of the 5th, 7th, and 8th are “trimmed up” to 49,000 points each, so the stay costs 3,000 points more than it would if the nightly rates were used. But because the night of the 9th costs so much more, the total cost of the stay is still less than the previous example.

Why does Hilton use this hybrid model?

The truth is, I’m not sure why Hilton has adopted this pricing model. And in fact, I’m not even certain that they did it deliberately. It’s perfectly believable that they price five-night reservations this way for reasons totally unrelated to the fifth-night-free benefit. Perhaps another day I’ll try searching for five-night stays in a new account without elite status to see if the pricing change is function of stay length and not trying to nickle and dime points redemptions after all.

If I did have to guess (we’ve now entered the reckless speculation portion of the post) I’d say that this was probably not actually designed to rob a few thousand points from their most loyal customers here and there, but rather to “simplify” the pricing page. The main visual effect of Hilton’s “trims” is to bring each of the four remaining nights closer together in price.

Here’s another set of examples where rates are trimmed up (against the customer):

And here are some dates and room types where rates are left as is, giving the customer the “full” 60,000-point credit for the last night:

In other words, what looks to us like a pricing decision engineered to get one over on us may have been as simple as a developer trying to think of a kludge that would make all the numbers look more or less the same.

Why it matters

While I’m sure there are folks as interested in the minutiae of pricing decisions as I am, the concrete reason this practice matters is that Hilton frequently sells points for “a bit less” than 0.5 cents if you first click through an online shopping portal to Points.com.

This isn’t usually an especially good deal, since Hilton points are also worth about 0.5 cents, and it doesn’t make any sense to buy anything for what it’s worth; keep your money.

Buying points for an immediate fifth-night-free redemption is an obvious exception. If you can buy $1.25 for a dollar, then the proposition becomes a lot more interesting, but only if you know how many points to buy.

And this is, sure enough, exactly how I got interested: I bought points for a five-night reservation, and once the points had hit my account discovered I didn’t have enough, because the Hilton website will not show you the total cost of an award stay unless you have enough points to book it (the iPhone app will if you click on “rate details”). Hilton had “trimmed up” the cost of my stay, and I had to buy a few thousand more points at a penny each to get over the top.

Can Hyatt promo codes override seasonal cancellation policies?

Over the New Year holiday I braved the madness that is flying Southwest Airlines and took a weeklong trip down to Playa Del Carmen, Mexico. While putting the trip together, I noticed something curious as I sifted through the hundreds of hotels lining Quintana Roo’s coast: using a Hyatt promo code seemed to remove the restrictive cancellation policy at the hotel I ultimately chose. Since I didn’t need to cancel the stay, I’m not certain this is replicable or even useful, but I wanted to put the possibility on readers’ radars.

Planning my stay

Sparing the details of how I narrowed down the options, I finally settled on the Thompson Playa Del Carmen Main House, which had a nice combination of being both “in town” as opposed to the isolated beachfront resort hotels and a Hyatt property which at 15,000 points per night was an order of magnitude cheaper than any other hotel I was seriously considering.

The plan was complicated, in a good way, by the fact that I had two stackable American Express Offers, one for $60 off $300 spent at any Thompson in the world, and the second for $100 off $400 spent at any Hyatt property in Latin America. I also had over $1,000 in Hotels.com gift cards I got from Cardcash in an earlier gift card exchange.

This meant I wanted to break my weeklong stay into three pieces: paying for the most expensive nights with Hyatt points and a free night award certificate, paying for the cheapest night with my American Express card in order to trigger $160 off $400 (I used room charges to “top up” my bill to $400, since the cheapest of the 7 nights was only $379.90 after tax), and paying for the remaining nights using my Hotels.com gift card.

Cancellation policies, promo codes, and “Pay Your Way”

Since I was looking for the cheapest night to pay with my American Express card, I started on my irregularly-updated Hotel Promotions page and saw that the promo code “GOJALIN15” was offering up to 15% off paid stays. When I plugged that code into Hyatt’s “Special Offer Code” field, the rate popped right up.

This Thompson property, at least between Christmas and Epiphany (apparently a big deal in Quintana Roo), had a 30-day cancellation policy on award reservations and on all the normal paid rates I found. Inside of that 30-day window, no changes or cancellations were permitted without forfeiting the entire price of the stay.

The GOJALIN15 rate did not have that restriction. Instead, it had the standard 3-day cancellation policy you’ll find on stays if you go searching right now. This wasn’t particularly interesting on its own: I only wanted to book one night with cash, and the 30-day cancellation rate was much cheaper than the GOJALIN15 rate.

What got my attention was that when I clicked through the GOJALIN15 rate, I was offered the ability to “PAY MY WAY,” Hyatt’s booking feature that allows you to combine paid nights and award nights on a single stay. And using that option, the favorable cancellation policy passed through to the PAY MY WAY booking page.

Two observations follow from this, one actionable, the other merely interesting. The interesting point is that some (or all!) coupon codes generate PAY MY WAY-eligible rates; typically only "standard” and “member” rates are eligible for PAY MY WAY, so it’s nice to be able to identify potential future exceptions.

The more practical consideration is that if you plan to redeem points for a stay with unfavorable cancellation conditions, but can use a coupon code that applies more generous terms to the whole stay, then you might be able to “buy” a more flexible cancellation policy by paying for one night of the stay with cash.

Additional considerations

That’s the potential play, as far as it goes, but there are two more wrinkles.

First, it seems that even if you use PAY MY WAY on a coupon code with favorable cancellation terms, if you pay entirely with points or award certificates, then the stay is treated entirely as an award stay and the cancellation terms revert to the standard ones after making the reservation. In other words, you can’t change the cancellation policy on an award reservation merely by clicking the PAY MY WAY button.

I say “after” making the reservation because all through the booking process the more generous coupon code terms were shown. It was only after making my reservation and receiving the confirmation e-mail that I saw the 30-day cancellation policy on my reservation. I think this gives you a pretty airtight case for having the more favorable terms manually applied, as long as you are sure to take plenty of screenshots during the booking process.

Second, because I didn’t ultimately make a “mixed” PAY MY WAY reservation, I don’t know if the same thing would have happened in that case. If so, I still think the case for invoking the “original” more generous terms would be ironclad, but it’s never ideal to get into a position where the score is up to the ref.

Conclusion

I’m aware that what I’m describing is a fairly advanced corner case. You need to have a working coupon code that is set up with favorable cancellation terms (GOJALIN15 expires February 28, 2024), a property with unfavorable cancellation terms during your stay, and a stay with at least one paid night cheap enough to justify paying in cash to swap the cancellation policies — plus the willingness to fight for your points back if you do need to cancel the reservation in the window between the favorable and unfavorable policies.

And if you don’t ultimately cancel the reservation, then you’ll never know whether it “worked” or not!

Hilton gift cards trigger American Express Surpass statement credits

In October, 2023, American Expressed announced changes to the Hilton Aspire and Surpass co-branded credit cards. American Express has acquired a well-deserved reputation as a “coupon book,” and these changes were no exception. Alongside an increase in the annual fee from $95 to $150, American Express added “up to $50 in statement credits each quarter for purchases made directly with a property in the Hilton portfolio.” The only question was, how easy would it be to trigger those statement credits?

Hilton gift cards trigger Surpass statement credits

Back in December I tweeted that I’d received the $50 statement credit for the fourth quarter for purchasing a $50 Hilton gift card. Since the first quarter of 2024 was just around the corner, I decided to wait to write a blog post until I’d replicated that experience. This is that blog post.

Interestingly, the gift card purchase also triggered the Surpass’s 12 points per dollar spent on “eligible purchases made directly with hotels and resorts within the Hilton portfolio.”

Timing

I purchased my first $50 gift card on November 23, 2023, and my first statement credit posted on December 2, 9 days later. I purchased my second $50 gift card on January 1, 2024, and the second statement credit posted January 10, again 9 days later.

Having established that pattern, do not worry if your statement credit still has not posted 8 or fewer days after making your gift card purchase!

Why does it work?

All I can do here is speculate, but there are two obvious explanations.

First, it’s possible that when Hilton set up their gift card provider, they explicitly coded it as a Hilton property. If gift cards were coded as regular spend, earning just 3 Honors points per dollar, there would be a real tradeoff between putting your hotel spend directly on your card versus paying with a gift card. Coding gift cards as Hilton purchases eliminates that tradeoff.

The second possibility is that when American Express coded the $50 statement credit, they used a simple filter for the word “HILTON” in transaction descriptions. Since gift card purchases post as “HILTON GC [STRING OF NUMBERS]” they trigger the credit. This raises the interesting possibility that, for example, purchases made in Hilton Head Island, South Carolina, would trigger the credit if the merchant included the town name in their credit card description!

The cards themselves

Perhaps fittingly given the relationship between American Express and Hilton, the gift cards take the form of American Express cards, in the sense that they have 15-digit card numbers starting with 3, and can be used at any Hilton property that accepts American Express.

Whether the cards can be used at non-Hilton merchants that accept American Express is an exercise left to the reader.

Conclusion

Each $50 Hilton gift card has a $1.95 shipping and handling fee, so purchasing $200 in gift cards per year raises the total annual cost of the card (including the annual fee) to $157.80. In order to break even, you therefore need to value Hilton gift cards at about 79 cents on the dollar. Whether that’s a high value or a low value depends on how you plan on using the cards.

From my perspective, 79 cents is “a bit high” for spending the cards on food and drink at Hilton properties, since hotel prices are typically marked up by more than 25% off street prices, so I rarely spend money at hotel restaurants.

On the other hand, 79 cents is quite low if you plan on using the gift cards to “pay down” your hotel room charges, whether for your room rate on paid stays or, for example, for resort or other ancillary fees that you’d otherwise have to pay with cash. While resort fees should be waived on award stays, some resorts (like the Maldives resorts that have launched a thousand blog posts) charge hundreds of dollars in transfer fees that should be eligible for payment with Hilton gift cards. A 21% discount on those fees is likely better than anything your credit card offers, unless you’re spending towards a particularly lucrative signup bonus and have limited manufactured spend opportunities at home.

My successful experience replacing an Incomm Visa prepaid card

There is, by all accounts, an epidemic of fraud striking prepaid debit card retailers across the Western United States. I’ve had the remarkable good fortune of never encountering a tampered prepaid debit card in the wild. So when I needed an Incomm prepaid debit card replaced this month, I jumped at the opportunity to find out how the process works in practice.

Fraud has become a huge problem, but not my problem

If you visit manufactured spend forums you quickly find an ocean of complaints about gift card fraud. Not the “elder abuse” fraud that newspapers love to write about, but genuine larceny: card packaging is opened, the details of the card are swiped, then the card is repackaged so that when an unsuspecting customer activates the card, the balance is quickly drained by the fraudsters. I don’t have a representative sample but it sounds like there are at least some stores on the West Coast where almost every card seems to have been tampered with.

This was not my problem. My problem was that I messed up the magnetic stripe on a card. In other words, user error. Since the balance was still there and I had the card details, I could have liquidated the card online for a tax payment, or to reload my Amazon balance, but instead I called up Incomm to see what the process was to replace the card.

Incomm prepaid card Replacement process

When I realized my error, I first called the number on the back of my Visa prepaid card (833-322-6760). During that call, which according to my phone lasted 17 minutes, I provided the usual card information, as well as the prepaid card’s “serial number,” which is located on the bottom right quadrant of the back of the card, as well as on the card packaging. The phone representative also asked for my name and address. Finally, he asked me to send “copies” of the receipt, the front and back of the prepaid card, as well as my government ID, to “consumed@incomm.com”. I took photos of the documents using my phone on my dining room table.

I first sent the documents on Friday, December 1, 2023, and on Monday, December 4, I received an e-mail from the same address asking for copies of the front of the card and the receipt again. I immediately submitted new pictures.

On Monday, December 11, I received a new card via USPS first class mail. That card had to be activated over the phone, which according to my phone records took 1 minute. I had the option to set a PIN over the phone or use any 4 digits on the new card’s first use, like a normal Incomm prepaid debit card. The card could be and was immediately liquidated through one of my usual in-person channels.

Conclusion

Obviously I wasn’t going to freak out over holding a card for 10 days instead of my usual 90 minutes, but despite my story being anti-climactic there are some obvious lessons you may need a refresher on if you’ve gotten lazy in your manufactured spend routine:

1. Keep your cards, receipts and packaging together. You can use filing cabinets, ziplock bags (guilty) or anything else you like, but if you get a fradulent or defective card you will want to be able to pull everything out at once without having to triple check card numbers and your purchase dates and times. Any unforced errors you make are going to slow down the replacement process.

2. Act quickly. In the case of tampered cards this is more important, but even if you mess up your own card, Incomm isn’t going to replace it until you contact them. Set aside 20 minutes and pick up the phone.

3. Don’t float more than you can afford to. I got stuck with $500 in the ether for 10 days, which didn’t bother me because it was a short period and a reasonable amount. If I’d just bought $10,000 worth of cards and needed them all replaced before my next credit card bill was due, I’d have been sweating a lot harder!

Leaving money on the table: you can use Railcards for Heathrow Express, too

I was playing around doing some research for my recent posts on my trip to the United Kingdom and made a discovery that left me equally pleased (that I get to share it with you) and frustrated (that I didn’t realize it at the time): you can and should use Railcards on the nonstop Heathrow Express service between London’s Paddington Station and Heathrow airport. It’s not exactly “tricky,” but you do need to know what to look out for.

As a brief refresher, Railcards offer savings on all National Rail services in Scotland, England, and Wales. They can be purchased online in advance, are typically valid for between one and three years, and they are virtually never checked by conductors on-board (although supposedly if you get caught without the applicable Railcard you have to pay a “penalty fare” or buy a full-price ticket).

My error was simple, although hopefully readers will find it excusable: Heathrow Rail, despite only operating a single 15-minute route between two stations, still belongs to National Rail, and consequently Railcard savings do apply to these tickets — and the savings can be substantial.

Add your Railcard on the Heathrow Express search results page

Unlike the other National Rail booking engines I looked at, which allow you select your Railcard up front, Heathrow Express’s own booking page only allows you to add a Railcard after searching for tickets. You’ll find the option on the right-hand column of the search results page:

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Adding a Two Together Railcard to a £50 one-way itinerary reduced the price by £17 — over half the price of the Railcard itself, meaning the Railcard would pay for itself with a single round-trip ticket for two at that price.

Since Railcards offer a percentage discount, the savings are naturally lower on cheaper tickets booked further in advance, but the point is the same: if you’re traveling by rail in Great Britain, it’s simply irresponsible to do it without a Railcard!

Heathrow Express tickets can be booked through some (but not all) National Rail companies

In my previous post I highlighted how each National Rail booking engine differs in subtle ways, including how accurately they code the precise requirements for each Railcard. The example I used was that Greater Anglia correctly requires a child ticket to be added to a reservation in order to apply the Family & Friends Railcard, while Avanti West Coast would price out the discount with an itinerary consisting solely of adults (violating the requirements for that Railcard).

Once I realized Heathrow Express participated in National Rail, I naturally wondered if tickets could be booked through those other booking engines. The answer, it turns out, is “sometimes.” Greater Anglia and Northern Railway (which seem to share a backend, with only a modestly different branding), will not apply a Family & Friends Railcard to Heathrow Rail booking at all, but will apply a Two Together Railcard (I have a theory for this I’ll explain in a moment). Avanti West Coast will show schedules, but will not allow you to book Heathrow Express tickets at all.

When you can (and can’t) book Family & Friends Railcard tickets on Heathrow Express

It’s going to sound obvious once I say it, but it took me a few minutes to figure out so I hope you’ll indulge me: children under the age of 16 ride free on Heathrow Express (although they seemingly must be accompanied by an adult). That means when the third-party National Rail engines try to validate the conditions for the Family & Friends Railcard on Heathrow Express, it fails the requirement to purchase a children’s ticket!

Fortunately, when booking through Heathrow Express directly, they seem to have identified and fixed this issue. To test this, pick a date and search for 4 adults without a Railcard, 4 adults with a Family & Friends Railcard, and 4 adults plus one child with a Family & Friends Railcard.

In the first two cases the price is the same (because the Railcard’s conditions aren’t met), and in the third case the base price won’t increase (because children ride free) but the conditions of the Railcard are now met and the price drops by the expected 34%.

Conclusion

It would be tiresome to say that this illustrates the importance of interrogating systems by looking under the hood and examining how they really work instead of relying on the nonsense put out by their public-facing organs.

Instead, I’ll simply conclude that entry and exit from the Heathrow Express is automated, and no one is there to check whether you actually have a child, or a Railcard.

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Double booking into the same Delta award space

So-called “fare buckets” are a curious feature of the airline ecosystem. For the overwhelming majority of flyers, even frequent travelers, the wide-ranging alphabet of letters, usually shown in parentheses after the class of carriage, is simply irrelevant: most people book on some combination of convenience and price, or have little or no choice if they’re required to fly on tickets booked by their corporate travel office.

So fare buckets don’t matter at all — until they’re the only thing that matters. For example, American Express Delta Platinum companion tickets can only be used to book into the L, U, T, X, and V fare classes. If those fare classes aren’t available for the flight you want, you simply cannot use the companion ticket on that flight.

The other important use of fare buckets is for finding award space on foreign carriers, especially ones that won’t show you availability unless you have sufficient miles in your account. Expert Flyer has a paid service that allows you to see the inventory available in each fare bucket for hundreds of airlines.

It’s important to note that there’s nothing magical about fare buckets. There’s not a “fixed” inventory in each fare bucket that never changes. While I assume most if not all airlines assign inventory to fare buckets algorithmically, the algorithms were still written by humans. An algorithm might say, “if there are 6 or more seats available in First Class, make one available for awards.” If that award seat is then booked, the algorithm might run again and make another single award seat available. One of the Japanese airlines is famous for doing exactly this.

Double booking the last available seat on Delta

As I wrote last month, although I’d finally booked my outbound tickets to England with SkyMiles, the price in Mileage Plus miles had ticked back down to 30,000, and I hoped to cancel the Delta award ticket and rebook using worthless-to-me United miles.

Having successfully completed that switcheroo, and with my Delta award ticket instantly refunded, I turned to booking flights to Wisconsin for a June wedding. There’s a single nonstop flight per day, and I found a ticket available for 26,000 SkyMiles. Almost like the good old days! But when I confirmed the dates with my partner and started booking seats for two, the price had jumped to 28,000 SkyMiles each! A 4,000-mile penalty just for waiting a day to book?

You probably see where this is going: the lower-priced ticket was still available, but there was just one seat available in that fare bucket. When I searched for two tickets on a single search, I was shown the lowest fare bucket with two seats in it.

What to do? Well, as Derek Trotter would say, “he who dares, wins!” So I had my partner fire up her laptop and log into her own Delta account. With both of us searching for a single seat, we both saw the 26,000-mile award available.

We each selected a seat, plugged in our payment information, and gave it a dramatic countdown: 3, 2, 1, click!

And we both got the last 26,000-mile seat.

This is obviously, in one sense, an almost trivial anecdote. We both had 28,000 SkyMiles in our accounts so if either of our purchases had errored out with “this fare is no longer available” whoever lost would have restarted the search and forked over the extra 2,000 SkyMiles.

But upon a moment’s reflection, the opportunities begin to come into view.

First, there are lots of tickets that cost more than 26,000 SkyMiles! For example, a one-way flight to Maui from Los Angeles in First Class costs 66,000 SkyMiles on December 3, 9, and 10. But on December 9, only one seat is available for 66,000 SkyMiles — try to book two, and the price jumps to 85,000 SkyMiles each. More realistically for a travel hacker, that means 66,000 SkyMiles for the first and 85,000 SkyMiles for the second, still a difference of 19,000 SkyMiles.

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Second, lots of people travel in groups of more than two passengers. If scalable, for groups of 3 or more the savings start to look astronomical. A family of four might save 57,000 SkyMiles flying in First Class to Hawaii; almost the cost of the first ticket!

I think this is a pretty neat trick, but to bring down the temperature let me state the obvious caveats.

First, to simultaneously book awards you need multiple accounts with sufficient miles in each. For a lot of people in “two-player” mode that’s not a big deal, but if you’re trying to book your kids or parents who don’t play the game, you will quickly struggle to find enough miles in enough separate accounts. If you have friends or colleagues in the travel hacking community that’s a good option, although it will likely involve at least some Zooming and screen-sharing to make sure all the booking details are right for each passenger, plus getting the timing exactly right.

Second, I don’t know how scalable this is: maybe it works for two passengers but not three, maybe for three but not four. Presumably at some point when the cabin is actually full Delta will reject issuing the ticket, so it’s essential to select your seats (different seats!) during the checkout process to make sure there’s room in the cabin for everyone.

Finally, I have no idea if this works on partner or international awards. I was booking nonstop, Delta-operated domestic flights. Would connections break it? Would partner award availability break it? I simply don’t know.

Conclusion

Like everything in the travel hacking game, your mileage will vary. If anything comes from this post, let it be the recommendation to search for individual seats before you search for seats for your whole family, since whether or not this trick works for you, securing one or two low-level seats before paying more for more expensive seats is an easy way of saving miles anyone can enjoy.

While this trick almost won’t certainly work for everyone, on every flight, in every class of service, I wanted to pass it along because it worked for me.