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.

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[…] written before about some of the challenges I had during Million Mile Madness: A setback from Sears and Bumps in the road.  Some issues, though, popped up late in the game and I haven’t […]

[…] 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 […]

[…] 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 […]

[…] 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). […]


Yikes. It’s been over a week and the balance on my HI cards still shows only $49 remaining ($450 for Sears gift card plus $1 for hold).


Does any know whether we buy third party gift cards (like amazon, shell) with Lowes’ gift cards? Thanks!


Karen: No, Lowes won’t let you buy gift cards with their gift cards

[…] Million Mile Madness: A setback from Sears […]


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.


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.


MrWho: I’ve never heard of Sears banning anyone.
Mike: It sounds like you’ve been very unlucky with shopping portals. It might help for you to read this post:


What does #29 Mike mean???? I’m confused by the words and phrases.


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.


You don’t get banned from Sears doing this? I think I’ve read Wal-Mart bans you doing something like this.


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?


JD: Kohls is not on the list of merchants that accept the Home Improvement card so it probably wouldn’t work


I’ve had problems in the past with Sears points posting.