The Sears double dip roller coaster


Background: Sears used to be one of the most reliable online merchants for portal “double dips”.  A Sears double dip goes as follows:

  1. Click through an online portal to and buy gift cards
  2. Click through an online portal again to and use the gift cards to buy merchandise

Via the above process, it has long been possible to double portal rewards.  For example, when a portal offered 10 miles per dollar for shopping at Sears, you could double dip to earn 20 miles per dollar (not counting credit card rewards).

Sears double dip roller coaster

A few weeks ago, I posted “Is the Sears double dip dead for real this time?”  The reason for the post was that terms regarding shopping at Sears via portals had changed and seemed to prevent the double dip.  For example:

  • Discover Deals added the following exclusion: EXCEPTIONS: …gift card purchases and redemption
  • TopCashBack added: Cash Back is eligible on the sale of Giftcards. There will be no cash back awarded for the redemption of gift cards.
  • Cartera Commerce Portals (such as AA, United, Southwest; and many others) added: Not eligible on the portion of a purchase paid for using gift cards, gift certificates, or any other similar cash equivalents. Only products with “Add to Cart” button are eligible. For the avoidance of doubt, purchases of gift cards, gift certificates, and similar cash equivalents are eligible.

In the same post, though, I pointed out that portal terms are not always enforced.  So, I set about testing a number of scenarios.  I’ll provide the results below, but first you need to know that portal terms have changed again within Cartera Commerce Portals.

New portal terms

Discover Deals and TopCashBack have (so far) kept the terms shown above.  Cartera Portals, though, now state, in part:

Not eligible on purchase of gift cards as of 11/16/2015

Interestingly, the prior language excluding the use of gift cards is gone.  This is a complete about-face from the prior language that stated “For the avoidance of doubt, purchases of gift cards, gift certificates, and similar cash equivalents are eligible.”

If the terms were true…

I find it hard to believe that Sears is enforcing completely different rules between the 3 portals shown above.  However, if the terms are really enforced as stated, then we can still double dip:

  • Go through TopCashBack (or any portal in which the terms allow the sale of giftcards) to buy gift cards
  • Go through any Cartera portal to use the gift cards

Heck, we can even triple dip this quarter:

  • Go through TopCashBack (or any portal in which the terms allow the sale of giftcards) to buy gift cards
  • Pay for the gift cards with a Discover card enrolled in the 4th quarter 5% back promotion (Sears counts as a department store. Make sure to buy e-gift cards with the Sears logo in the front. Physical gift cards and some e-gift cards are sold by Kmart and will not trigger the Discover 5% bonus)
  • Go through any Cartera portal to use the gift cards

What is really enforced?

The Discover Deals portal seems to have been stuck in limbo since mid October.  Many people who made gift card purchases or regular purchases (no gift cards involved) through Discover Deals to any store, have yet to receive any notification of cash back from Discover (with one notable exception that I’m aware of).  This is very unusual since Discover used to send congratulations emails within a few days of each purchase.  So, for now at least, your only use of Discover Deals should be purchases that are explicitly allowed by the terms. That way you can always call and ask to be credited with the expected cash back if it doesn’t appear automatically.

Based on the above, it should come as no surprise that the many experiments I’ve run recently through the Discover Deals portal have been inconclusive.  I’ve failed to earn cash back so far on any purchases regardless of whether they met the portal terms or not.

In my recent experiments with Cartera portals, I found that all purchases using gift cards and/or Shop Your Way points did result in earning portal rewards.  Unfortunately, those experiments were run before the terms flip-flopped.  It’s now possible that purchasing gift cards through Cartera portals will not result in rewards.  More likely, I think, we’ll find that some types of gift card purchases work (such as e-gift cards), but some do not.

I’ll continue to test things out, but unless something surprising and interesting happens, I probably won’t post the results as a new blog post. Instead, I’ll post the results as comments in the Frequent Miler Laboratory.

Frequent Miler Laboratory

To find out what is currently working and what is not, head over to the Frequent Miler Laboratory page.  There you’ll find a table showing experiment results conducted by me and by many readers.  And, if you read through recent comments, you’ll often find results that haven’t yet made their way to the table.  If portal shopping is important to you, I recommend subscribing to the Lab comments (write “subscribe” and check the box “Notify me of follow-up comments by email”).

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Confirming Sears email bomb’d me last night with several confirmed CB on order, mostly GC redemption, but some GC purchases. I accounted for ~50% of my orders being confirmed.

What a ride, what a ride….


Also, all confirmed emails did not mention a date (transaction date and order ID marked as “not available”


Me too


Hey Greg,

Thanks for linking to the post. Since then I’ve gotten a bunch more emails confirming cashback from 30 days before. Have you still not gotten anything?


Seeing the apple pay 10%, also.


I am getting notifications from DC about CB when using their portal AND the DC. Also, seeing CB in account.


Shopathome gave me cashback for gift card purchases. It’s 6% now. nothing like what Discover used to be. 😉


I earned bonus miles by reloading sears GC after the term changes. Looks like it’s still safe at least for reloading a gift card.

So the new steps with cashback would be:

1. Use TCB and buy Sear giftcard from Sears? (2%)
2. Pay With Discover (10%)
3. Use Shop Through Chase since it’s Cantera (to use the gift card?) (4%)

So 16% back before you include and of the Shop Your Way Points. Am I correct in believing this?


Does Sears allow Sears gift cards as payment for other gift cards?

Nick L.

My concern is if they are asking to see invoices of your purchases, who is to say that they wont disqualify your purchase if you use a coupon code that is not approved by them.even if you use Discover Card through Discover Deals portal.

I know in the past they never enforced it but with the double cash back they may find any reason to not pay.


Fortunately I reload sears GC through AA portal on 11/15 and get miles. Yesterday I reload a small amount through Alaska Airline portal. I’m waiting to see whether I can still get miles from the reloading.