Million Mile Madness: A setback from Sears

746,000 points earned. 254,000 left to go.

Background: Million Mile Madness is the fun and foolish quest to earn a million points in one month. Throughout March, I’m doing everything I can to earn as many points as I can while keeping within my ethical boundaries. I don’t expect that a million points will have been credited to my account by March 31st: points often take quite a while to get credited. Instead, I’ll track all of the points that I expect, and I’ll declare victory if the expected total is over a million. To keep things challenging, I will try to keep my net costs below $1,000.

All points earned and expenses incurred are tracked via this Google Docs spreadsheet.

See all Million Mile Madness posts (in reverse order), by clicking here.

Points from Sears

Sears used to be my favorite retailer for collecting points.  They used to regularly run promotions in which they would offer 10 points per dollar through the Ultimate Rewards Mall, or 10 miles per dollar through the AAdvantage eShopping portal.  And, Sears used to give points when you purchased e-gift cards.  This combination was powerful.  It was possible to earn 11 points per dollar for buying e-gift cards (1 point from your credit card and 10 from the shopping portal) and another 10 points per dollar when using the gift cards for a total of 21 points per dollar for any purchase.

Sears no longer offers points for e-gift cards.  Worse, it has been 6 months since we’ve last seen 10 points per dollar from Sears.  More recently they’ve held more or less steady at 5 points per dollar through the Ultimate Rewards Mall and even less than that through other portals.  Given that, I was ready to take advantage of 5X through the following triple dip:

  1. Buy Home Improvement gift cards at Office Depot.  Pay with a Chase Ink card to earn 5 points per dollar.  See “The Home Improvement gift card” for more details.
  2. Go through Chase’s Ultimate Rewards Mall to Sears.  Use the Home Improvement card (as a Discover credit card) to buy Sears physical gift cards.  Earn 5 points per dollar (physical gift cards still earn points).
  3. Go through Chase’s Ultimate Rewards Mall to Sears again.  Buy merchandise and pay with the Sears gift cards.  Earn 5 points per dollar.

Through the above techniques, it would have been possible to earn 15 points per dollar shopping at Sears.  I’ve tested each of the above steps before and they’ve all worked perfectly.  In fact, this is the same process I wrote about previously for earning 15X at Lowes (see “Million Mile Madness: Banking on Lowe’s). 

Unfortunately, early in March, Sears dropped its payout in the Ultimate Rewards Mall to only 3 points per dollar!  That would have brought down the triple dip described above to only 11 points per dollar altogether. 

Luckily there have been other options.  From March 10 to March 12, Sears offered 6X through the AAdvantage eShopping portal.  And, currently, Sears is offering 6X through Southwest’s RapidRewards Shopping.  For various reasons, I didn’t take advantage of the AA 6X offer, but I did go for the Southwest 6X opportunity. 

I clicked through from the RapidRewards Shopping portal to Sears and bought a $450 gift card.  I paid with a $500 Home Improvement card, which is considered a Discover card.  The reason I didn’t try to buy a $500 card is that Sears places a $1 hold on the card to validate it.  So, the most I could do was buy a $499 gift card.  I decided on $450 because that would leave $50 on the Home Improvement card, which I could use later to buy a gas gift card at Lowes.

I went through the above process four times in order to buy a total of $1800 worth of Sears gift cards.  From this exercise I expected to earn 10,800 RapidRewards points.  My plan was that once I received the Sears gift cards I would go through a portal again to buy merchandise and possibly earn another 6X for a total of 17 points per dollar.

That was the idea, until Sears called…

A guy from Sears’ fraud department introduced himself and asked permission to verify a few things.  He told me that they get a lot of fraud with gift card purchases and so need to be careful.  He asked what type of credit card I used.  He asked how many cards I bought and for how much.  He then asked if it was OK if he called back in 10 minutes.

Ten minutes went by, and then twenty.  Then I received four emails that went like this:

Dear FM,

We are confirming that we have cancelled your order XXXXXX as you requested.

Ouch.  Back to Lowes I go.

Learn about Million Mile Madness:

About Greg The Frequent Miler

Greg is the owner, founder, and primary author of the Frequent Miler. He earns millions of points and miles each year, mostly without flying, and dedicates this blog to teaching others how to do the same.

More articles by Greg The Frequent Miler »


  1. […] New opportunities for manufactured spend continue to appear, but they are not always practical and may be risky. Wells Fargo had an option to load prepaid cards with a credit card, but that window is being shut down in May and risked cash advance fees and security reviews if you weren’t careful. Buying and reselling merchandise requires a large upfront cost, the risk you won’t earn it back, and the risk that the category bonuses you were relying on will be reduced (as Frequent Miler himself discovered with Sears). […]

  2. […] gift card, then read the comments section on this post by Frequent Miler.  I believe he has since had some issues with shopping online at Sears with this card.  I’m probably too boring to do anything crazy that is likely to get noticed, but keep his […]

  3. […] gift card, then read the comments section on this post by Frequent Miler.  I believe he has since had some issues with shopping online at Sears with this card.  I’m probably too boring to do anything crazy that is likely to get noticed, but keep his […]


  1. I thought Lowe’s didn’t allow gift card purchases with gift cards… I know the HI are technically Discover cards, but are they not viewed as gift cards when purchasing 3rd party GCs?

    • ZJ: Lowes see these as Discover cards. To use them you need to “Add a credit card” and select type = Discover
      DonT: I think they tried to verify my identity from the credit card used, but I had only been able to register my zip code with the HI cards. Plus, I used 4 different HI cards to buy 4 different Sears gcs. Must have looked suspicious.

    • Piecerate: I have to wait until $451 in preaths drops off of each card before I can do anything. At this point I think I’ll go all in with Lowes or cut my losses and use the HI cards to get high value gcs at Lowes to trade in to PJ or elsewhere

  2. @FM, you’re not going to try again with Sears? From the way you detailed it, Sears’ fraud guy didn’t seem that bad and you obviously didn’t WANT to cancel the order. Is there any harm in contacting Sears to try to re-instate/re-do the order?

    • Ben L: If I call to reinstate the order, I’m worried that the portal points wouldn’t track anymore and that would mean losing the point of doing this (no pun intended). To start all over, I have to wait about 3 days for the preauths to drop off the cards. Maybe I’ll try one card at that point if I can still find a good portal multiple for Sears

  3. This is kind of what I was meaning with my comments about lying about a move to Lowe’s. I guarantee if enough people try these things, the rewards programs will go away.

    Now, there probably won’t be too many people that start doing this, but when blogs like this started popping up I did start to worry about that a bit.

    Now, obviously there is nothing illegal about what you attempted. Fraud should be saved for people actually committing fraud. I see nothing wrong with buying gift cards and then using them in order to benefit.

    Recently was at Kroger and the guy next to me was pumping gas at some ridiculously low price, like $1.79/gallon. Turns out he is a contractor and he when he buys things for jobs he goes to Kroger and buys gift cards for Lowe’s and Home Depot. Then he uses the gift cards to purchase the items.

    Kroger gives him gas rewards for the amount he spends on his Kroger shopper’s card. Pretty cool.

  4. To Ben L, good point. Again this is NOT fraud and the fraud department had no business getting involved. Unless they have some terms of the program specifically saying you can’t do this.

  5. With your timeline you obviously can’t slow play thus, but as a general rule it probably makes sense to do smaller transactions and spread them out a bit. Your setbacks are as instructive as your successes. Thanks for the reports.

  6. The plot thickens and interesting to follow your story line. Sorry for your setback…hope to see you at the end of the 1 mil race.

  7. Great post. Learning from the mistakes is just as important as the successes. I wish I could get my grubby hands on that home improvement card. Think I’ll have to pick up a few next time I am in Fargo or Minneapolis.

  8. As soon as the cards clean up again from the cancelled transactions I would go back and try again at sears but slowly with one at a time over a period of several weeks and maybe use a spouses name or change your name slightly on the order, change your address just slightly, etc. You could be in the system now.

  9. I ordered 3 different gift cards using the above methods last month and due to some immediate need, I placed expedited shipping on all of them. The following day I got a phone call from the GC dept and they verified some info. But I received only 1 of the 3 cards on time and the rest 2 arrived 4 days later. Their order status shows absolutely incorrect information all the time. The order shows delivered and the UPS status shows in-transit. This is horrible stuff from
    But on the flip side, I got all my points for the gift card purchase and also for merchandise purchase which I cannot complain about.
    I have sent emails to Sears asking to at least refund my expedited shipping charges since I received the cards after a whopping 7 days.

  10. How long to ultimate rewards take to post if you use a non-Chase credit card? Specific stores are sears, officemax, lowes. I assume its not a problem to use a store promo code as long as its not a 3rd party.

    Similar question for Amex Open percentage credits – any idea how long they take to post?

  11. There fraud dept. always calls every time I have bought gift cards. They want to verify my identity and give my some b.s that fraud happens all the time. Well if my billing address and mailing address matches it must be me…

    Good job not pushing it, just reorder the items and try again.

  12. I got a call from their Fraud department when I purchased $2500 in gift cards for the SWA double-dip Companion pass, last may. He asked me some questions based on my credit report, and I received the e-gift-cards an hour later.

    I mean, buying $2500 in Sear’s gift cards is pretty suspicious, gift cards are an excellent way to cash out a stolen credit card, but I’m surprised they cancelled the transactions after talking to you.

  13. Interesting FM. I bought 1 $499 Sears GC during the AA 6X. 2 days later, I bought 3x$499 more. Then a day or two later, Sears called me to confirm that I actually did 4x$499 GC’s. I said YUP and she mailed it out. A month prior though, I bought 1x$499 and a rep called me to answer the 4 security questions like, “You lived in which of the following cities?” They never questioned the card I used to pay for the GCs. I know if you hadn’t bought a GC in a long time, they will call to ask the security questions again.

  14. Karen: I’m not sure
    Calvin: usually the UR mall takes 4 to 5 days to show points as pending. Sometimes it takes longer. Amex OPEN takes about a week to show up in my experience

  15. I had this happen when I purchased my TV in sept with the 10x point double dip. I called them after getting the please contact email.

    I just told them how annoyed I was that I kept getting security alerts from them. I bought 3 gift cards within a few hours for $1500. I got contacted all 4 times (for the gift cards and the final TV purchase) even after they supposedly put a note in the file that I had already been cleared on the first one.

    I did use an actual card vs buying gift cards with a gift card though. Despite the hassle I did end up with 30k UR points.

  16. I wonder if this technique could be applied to Kohl’s as well, ie, buy lowes gc at office supply stores; buy physical Kohl’s GC; buy Kohl’s merchandise. Any idea?

  17. After being introduced to your world back with the 15 next Southwest last year I partook in a bunch of Sears business thank the incidents on business that they made me an elite VIP member. However back in September when there was a text for you bemusing a Chase freedom card through the Chase freedom portal they didn’t track nor acknowledged that I should be given my points even when I presented them with screen captures because I have been burned in August through the bold card over 5 to 10,000 points but in September it was a question of about 20,000 points. Come October with just my luck I would say about 10 orders only about three or four track and those are all ones that sears eventually canceled because they were out of stock so they clawback a lot of my points and then fast forward to November 17 when I had a VIP bonus day, I spent around $5000 all on credit card this time because wait to many gift cards were tracking and it didn’t count a single one through ultimate rewards, but 1 order for $250 on a GC through SW counted. In January I redeemed Milta rewards for gift cards so I have physical gift cards and redeem $1700 worth and didn’t get a single point for that either. Then on my last VIP day on February 23 I spent $8000, $5000 on Chase cards alone not a single one tracked. They did however start cleaning so many of my orders were online returns when fact they weren’t but it’s because Sears system never updates my delivered items from processing to deliver have the time and after six weeks they claw back the points so now I have -20,000 points. After making a quick tally of what they owed me I actually got screwed out of about 100,000 points in tracking easily…. And that’s without me double dipping because I entrusted cards anymore double-dip would’ve been a nice 200,000. At this point everyone the only possible thing is the worlds and a quarter Ebola stays that give me 5 to 15% of chop your waypoints which are used to just buy merchandise and so but obviously worthless when it comes to renting for airline miles through Ultimate Rewards. My spend for 2012 was $29,000 at sears and so far this year it’s 10,000 so conservatively factoring in our use the doublie dipped and I was 10 points and six points and five points I should at least have assuming around 7 pts avg 280,000 miles (actual calc was 520,000 expected but I got a measy 170,000 points. So I don’t know how you guys doing Chase because I stop double dipping stop using other cards and even with the Chase cards they flat out denying the points every other portal and every other store will work just fine.

  18. I’ve had Sears fraud dept call me on a $23 purchase with the Home Improvement card. It took quite awhile on the phone to get them to accept it.

  19. FM: I notice on your spread sheet you took the paypal cash instead of a check from PJ on your pie day gift card churn. Any reason in particular? Also, do you have a safe way to liquidate paypal? I’ve always read that paypal can be pretty harsh with withdrawals.

    • Larry: I’ve used PayPal for years mostly to move money from one bank account to another and I’ve never had any trouble with withdrawals. I keep a balance in there so that PayPal can still profit from my business.

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