Is the Sears double dip dead for real this time?


Sears used to be one of the most reliable online merchants for portal “double dips”.  A Sears portal 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).

The Sears Double Dip became a bigger deal than ever before when Discover started offering double rewards for a year to new card members.  This quarter, Discover is offering 5% cashback at and department stores (including Sears).  And, the Discover Deals portal is offering 10% cash back for clicking through to  Via the double dip, plus the 5% credit card rewards, it would be possible to get a total of 25% back which would then eventually double to 50% back!

That is, 50% back would be possible if the double dip was still alive…

In late August, the Sears double dip appeared dead when Sears changed their terms within many portals to state “Not eligible on gift cards, gift certificates or any other similar cash equivalents.”  After some experiments, though, it looked like Sears was not enforcing the new terms.  Gift card purchases were still resulting in portal rewards despite the new terms.  See: The promo of the year lives on.

Terms change again

The terms introduced in August, “not eligible on gift cards” were unclear.  What did that mean?  Did it mean that you wouldn’t earn portal rewards for buying gift cards or for using gift cards?  Was it specific to certain types of gift cards?  Maybe it meant that you wouldn’t earn rewards for buying 3rd party gift cards.  After all, when you go to the gift card page and scroll to the bottom, you see this:

Sears double dip SearsGiftCardMall

Maybe it was saying that purchasing Gift Card Mall gift cards that were ineligible?  Note: I can confirm that you do not earn rewards when buying these.

Recently, Sears’ portal terms changed again in a number of portals.  Here are some examples:

Discover Deals

EXCEPTIONS: In-store pickup, ShopYourWay partners, Sears auctions,,,,, PartsDirect, Home Services,, gift card purchases and redemption, layaway, shipping, taxes and other service fees


Please note: 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 (this includes portals for most airline programs such as AA, United, Southwest, Delta, etc.; some bank portals such as Chase; and many others)

Not eligible on purchases made with coupon or discount codes that are not found on this site. 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. Not eligible on Home Delivery Charges, Services, PA and Installation, Master Protection Agreements, Take With, Protection Plans, Sears auctions,, PartsDirect, Sears Canada, Portrait,, or Outlet purchases. Not eligible on Sold by Kmart items or any other licensed partners. Not eligible on Apparel Clearance. Any return, exchange or other adjustment made at a physical store location for an on-line purchase may result in your purchase being deemed ineligible. Not eligible on online purchase made using Sears Shop Your Way points.

What does it all mean?

At first glance, the terms shown above seem to be clear.  With Discover, you will not earn portal rewards if you buy or use gift cards.  With TopCashBack, you’ll earn rewards for buying gift cards, but not for using them.  Cartera is the most specific: the portion of a purchase that is paid for with a gift card will not earn rewards.  However, purchases of gift cards will earn rewards.

TopCashBack and Cartera use different words, but at least they seem to be saying the same thing: get rewards for buying gift cards, but not for using them.  Discover says not to even breathe in the direction of gift cards if you know what’s good for you (I’m paraphrasing a bit).

Regardless of which portal you go with, there is a lot left unspecified.  In the distant past, when Sears explicitly disallowed gift cards, they enforced the rule for the purchase of e-gift cards but not for by-mail gift cards or gift card reloads.  So, when Discover disallows the purchase of gift cards, do they mean all gift cards?  Do some work, but not others?

What about the use of Shop Your Way (SYW) points?  You can earn SYW points by shopping at Sears, Kmart, Lands End, and a variety of other partners.  When you spend those points on merchandise at Sears will you earn portal rewards?  The Cartera portals say “Not eligible on online purchase made using Sears Shop Your Way points” (but I previously found that they didn’t enforce this).  Discover Deals and TopCashBack currently have nothing to say about SYW points.

What works, in practice?

It’s good to know what the portal terms state, but it is often the case that rewards are paid out despite the explicit terms.  Unfortunately, the only way to know if something works is to try it.  We do have years of experience in testing Sears double dips (as reported in the Frequent Miler Laboratory), but, for purchases, we need to throw out those results and start anew.  Whenever the portal terms change, there is a good chance that the behind the scenes coding has changed as well.

To get started anew, here are recent results reported via the Frequent Miler Laboratory, and elsewhere (dates shown are the date of purchase):

Result summary

Through October 6, it appears that everything was working fine. People reported success both buying and using Sears gift cards through the Discover Deals portal. I’m ready to chalk up my failure to receive cash back for my 10/1 order as an anomaly. Beginning October 7th, things become murky.  There were many reported failures, but most were based on waiting a week or less for results.  In my experience, the time between making a purchase and receiving a “Congratulations”,  email from Discover usually takes just 2 or 3 days.  However, with other portals I’ve had it take over 3 weeks, especially when large purchases were involved.  It’s possible that Sears or Discover Deals is simply taking longer right now to report these transactions.

If we filter to the failure reports in which people waited at least 3 days, and look only at the results beginning on 10/7, we can sum up the results as follows:

  • Reload gift card: Mixed results. Between 10/7 and 10/13, there were 9 reported failures.  Between 10/9 and 10/11 there were 3 reported successes.
  • Purchase e-gift card: All failed.  Between 10/12 and 10/13, there were 3 reported failures and no reported successes.
  • Buy merchandise with gift card (or partially with gift card): Mixed results.  Between 10/9 and 10/13 there were two reports of failures to earn any rewards when a portion was paid with a gift card.  Between 10/9 and 10/11 there were 3 reported successes.

Result analysis: Reply hazy try again

The results from above are so mixed, that there is very little we can say for sure.  My guess is that the following statements are true:

  • Guess 1: Sears is currently taking longer than usual to confirm purchases with the Discover Deals portal or perhaps technical issues have caused a number of purchases to go unrewarded this month.
  • Guess 2: Gift card reloads still work with all portals
  • Guess 3: E-gift card purchases no longer work with Discover Deals, but do work with other portals
  • Guess 4: Physical gift card purchases work with Discover Deals and other portals
  • Guess 5: Buying merchandise with gift cards still works through Discover Deals and other portals
  • Guess 6: Buying merchandise with SYW points still works through Discover Deals and other portals

New experiments in progress

To test the guesses listed above, I launched new experiments:

  • Via Discover Deals, I reloaded a gift card (Guess 2 says it will work)
  • Via Discover Deals, I purchased an e-gift card (Guess 3 says it will not work)
  • Via Discover Deals, I purchased a physical gift card (Guess 4 says it will work)
  • Via Discover Deals, I purchased merchandise entirely with gift cards (Guess 5 says it will work)
  • Via Discover Deals, I purchased merchandise with a combination of gift cards and credit card (Guess 5 says it will work)
  • Via Discover Deals, I purchased merchandise entirely with SYW points (Guess 6 says it will work)
  • Via a Cartera Portal (United), I purchased merchandise entirely with gift cards (Guess 5 says it will work)
  • Via a Cartera Portal (United), I purchased merchandise with a combination of gift cards and credit card (Guess 5 says it will work)
  • Via a Cartera Portal (United), I purchased merchandise entirely with SYW points (Guess 6 says it will work)

Next week I should be able report preliminary results.

Summary portal terms have changed.  As a result, we don’t know whether the Sears gift card double dip works any more.  The terms stated in the portals indicate that the double dip will not work, but terms are not always enforced.  Experiments reported by readers have been inconclusive so far.  I’ve launched a series of experiments to try to try to figure out exactly what works and what does not.

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