The promo of the year lives on


UPDATE 9/14/2015: Updated experiment results listed below

This year’s best promotion has little to do with airline miles or hotel points.  Instead, it comes from Discover.  In particular, Discover promises to double all cashback earned for 12 months by new Discover It cardholders.  This is a nice perk for those who would otherwise earn 1% cashback from the card for regular spend and 5% cashback for spend within Discover It’s rotating 5% categories.  This is a fantastic perk for those equipped to take advantage of the Discover Deals cashback shopping portal.  By stacking shopping opportunities it’s possible to earn 50% or more cashback for purchases you would have made anyway.  Then, when redeeming Discover Cashback, it’s possible to get more than face value by redeeming for discounted gift cards.  As I’ve written about before, my favorite option is to get $40 National Car Rental gift certificates for $20 each in Discover Cash Back.  Honestly, though, I’ve earned so much Discover Cashback lately that I can’t possibly use it all on car rental certificates.  Instead, I expect that I will redeem most of the cashback for regular old statement credits.

Sears quadruple dips

The ability to double, triple, or quadruple dip portal rewards (as described here) depends on a lot of things going right:

  • For a double-dip, an online merchant must allow earning portal rewards for both buying and using store gift cards.
  • For a triple-dip, the same online merchant must fit into a category in which Discover It offers 5% cashback.
  • For a quadruple dip, the same merchant must offer store rewards and must allow earning portal rewards when store rewards are used to purchase merchandise.
  • For all of the above, the portal in question (i.e. Discover Deals) must allow earning portal rewards even when their credit card is not used to make the purchase.

Regarding the last point: the Discover Deals portal’s terms do suggest that you must pay with your Discover card to to earn cash back.  In practice, however, I’ve earned cashback countless times despite using other forms of payment (e.g. I’ve used: other credit cards, or gift cards, or store rewards).

CAUTION: Some readers have reported having their cashback “clawed back” by Discover due to not having paid with their Discover card.  This may be true, but I actually think that a more plausible explanation is that cashback was clawed by by the merchant in question when the merchant realized that the order was not eligible for portal rewards, and/or when items were returned.  In those cases, it would not be surprising if a Discover customer service agent thought that the reason had to do with the form of payment.

Regarding the first three points above, Sears is the only merchant I know of that has reliably fit all three criteria.  Recently, though, new developments put the reliable old Sears’ double, triple, and quadruple dips into danger…

Sears backs off rewarding purchases of gift cards or purchases made with points

Sears recently added new language to their terms on a number of portals.  We first wrote about the changes here: Warning: Portals No Longer Paying for the Purchase of Sears Gift Cards.  Not only did Sears add language stating that buying gift cards wouldn’t earn rewards, but they banned earning rewards when using Shop Your Way points as well.  The new language, as found on a number of portals, states:

Not eligible on online purchase made using Sears Shop Your Way points. Not eligible on gift cards, gift certificates or any other similar cash equivalents.

Even though this new language showed up only on Cartera portals (which includes most airline mileage portals: AA, United, Southwest, Delta, etc.), we wrote:

Sears generally handles all portals the same way, so the ones without the gift card exclusion are probably just slow to update

and, in another post, we wrote:

Even if some portals do not yet have language like this, it is likely that they will work the same way as portals that do have the new terms.


In the post, “Sears nixes portal rewards on gift cards. There may be hope yet,” I pointed out that Sears used to have similar language against gift cards but that it wasn’t consistently enforced.  More specifically, it was enforced for e-gift cards, but not for physical by-mail gift cards and not for gift card reloads.  Clearly, it was time to experiment!

In order to see what works and what doesn’t, I selected three portals and made four separate purchases after clicking through each one.  In total, I made 12 test purchases to see which would result in portal rewards and which wouldn’t.  Here were the tests, all of which were conducted on September 1:

United MileagePlus Portal (a Cartera portal):

  • Click through portal to Sears and buy $10 physical gift card. Pay with Discover It card.
  • Click through portal to Sears and buy $11 e-gift card. Pay with Discover It card.
  • Click through portal to Sears and reload gift card with $12. Pay with Discover It card.
  • Click through portal to Sears and buy $13 item with SYW points

Southwest Rapid Rewards Portal (a Cartera portal):

  • Click through portal to Kmart and buy $10 physical gift card. Pay with Discover It card.
  • Click through portal to Sears and buy $11 e-gift card. Pay with Discover It card.
  • Click through portal to Sears and reload gift card with $12. Pay with Discover It card.
  • Click through portal to Sears and buy $13 item with SYW points

Discover Deals Portal (not a Cartera portal):

  • Click through portal to Sears and buy $15 physical gift card. Pay with Discover It card.
  • Click through portal to Sears and buy $11 e-gift card. Pay with Discover It card.
  • Click through portal to Sears and reload gift card with $12. Pay with Discover It card.
  • Click through portal to Sears and buy $10 item with SYW points

Of the three portals tested, the Discover Deals portal is the only one without language on the Sears’ page prohibiting rewards on purchased gift cards or with the use of Shop Your Way points.

I made sure to vary the dollar amount of each purchase through a given portal so that it would be clear which purchases earned rewards and which did not.


UPDATE 9/14/2015: All of the MileagePlus portal points are now showing as pending.  3 out of 4 Southwest Rapid Rewards portal points are also now showing as pending.  The only experiment that has not resulted in pending points is the purchase of items from Kmart using Shop Your Way Rewards points.

The results are pretty simple.  None of the purchases made through the Cartera portals tracked.  However, all of the purchases made through Discover Deals tracked.

I received the following email from Discover Deals on September 3:

Sears quadruple dips

On September 1, I had made a total of $48 worth of purchases from Sears through the Discover Deals portal.  The portal at the time was offering 5% cash back, so: 5% of $48 = $2.40.  That’s the exact amount reported.

Neither MileagePlus Shopping nor Southwest Rapid Rewards Shopping show any pending rewards on my account.  That’s not proof that the portal purchases didn’t work.  Sometimes portals can take weeks before reporting rewards.  However, the quick turnaround on my Discover Deals purchases suggests to me that I would have heard by now from the other portals as well.

All of the above results have been reported within the Frequent Miler Laboratory.

Wrap Up

Amazingly, Sears appears to be rewarding purchases made through portals exactly as stated in the terms.  That is, of the three portals I tested, the two that explicitly disallow rewards on the purchases of gift cards or with SYW points seemed to enforce those conditions (note that, despite the wording of this sentence, I believe it is actually Sears that enforces the conditions, not the portals).  The one portal that I tested that did not have the same language, Discover Deals, did report rewards for all four test purchases.

What this means:

Within any portal, pay close attention to the terms listed for the particular store in which you want to shop.  Not all portal / store combinations enforce those terms exactly, but Sears appears to do so at least with the three portals I tested.

For the Discover Double Cash Back for a Year promotion, this means that we’re still in business!  Unless / until the Sears terms change within Discover Deals, double-dip, triple-dip, and quadruple-dip opportunities will continue.  And, I think it is very likely that Discover Deals will increase Sears cash back to 10% in early October.  We’ll see!


  • There is always risk that Discover may take back cashback awarded when a Discover card is not used for a purchase. This would affect purchases made with gift cards or with merchant points (such as Sears’ SYW points).
  • If you are not awarded cashback when using a form of payment other than your Discover card through Discover Deals, you will not get help from Discover’s customer support.
  • Sears’ terms may change at any time.
  • Sears may change how they enforce the terms at any time.
  • All of my tests were with very small purchases.  While it’s unlikely, its possible that results would differ with much larger purchases.


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