A frustrating yet successful morning rolling points

Yesterday morning, I checked Sears and Kmart to see if there were any new 100% back in points offers.  I hit the jackpot at Kmart in the Weekly Member Deals section of their website, and  I reported my findings via Quick Deals.

rolling points

In the post “Roll gift cards into points for triple rewards” I explained in detail why deals like these can be worth pursuing.  The basic idea is that its possible to get portal rewards three times: once when buying gift cards, a second time when using those gift cards to buy 100% back in points items, and a third time when using those points to buy stuff you actually want or need.  The fact that my Discover It card is enrolled in Discover’s Double Cash Back promotion, makes this all the more appealing.

It is often the case with 100% back in points deals that few items are available for shipping.  Instead, you have to get lucky and find that the item is available at a nearby store for pickup.  This time, though, I found that nearly all of the Vivitar items were available for shipping.  And, there were a lot of them.  I started adding items to my cart, but soon found that there was far more available to buy than I had available in Sears gift cards.  I went ahead and bought what I could, then turned my attention to buying more Sears gift cards.

Items offered for 100% back in points always sell out quickly.  I had to hurry.

Buying Sears gift cards… quickly

Sears offers a number of ways to by gift cards: by mail, by email, printed, and by reloading existing gift cards.  In the past, I’ve found reloading existing gift cards to be the fastest option.  I did the following:

  1. I clicked through Discover Deals to Sears.com
  2. I found the option to check my gift card balance and reload.
  3. I added $500 to a gift card.
  4. I paid with my Discover card (which is registered to this quarter’s 5% Home Improvement and Department Store category).

After going through the above steps, I decided that I needed more than $500, so I repeated the entire process and loaded up a second gift card.  As expected, after that process, the gift cards still had no value.  It takes a while for Sears to process these orders and they usually call to verify your identity with large gift card orders.  As recommended in the Frequent Miler resource page “The complete guide to Sears gift cards,” I called 1-888-396-5299 to expedite my gift card order.  Still, almost an hour passed before the gift cards were actually loaded up.

Loading up my Kmart cart

Luckily, even though I had to wait a while to get my gift card credit, the 100% back in points items were still available.  I found that Kmart would let me add up to 3 of each item to my cart.  So, I systematically went through all of the Vivitar items and added 3 of each to my cart.  On the shopping cart page, I verified that the value of the points I would earn was equal to the pre sales-tax cost of items in my cart.  Then, I proceeded to try to add lots of Shop Your Way coupons to my order.  At first, a couple of coupons seemed to apply, but later it looked like they didn’t apply.  I was bummed about that because I had a coupon to get 15% back in points for electronics.  That would have been an awesome way to get more than 100% back in points.

Trying to check out

After playing with coupons for a while, without any luck, I clicked through to the payment screen.  There I noticed that Kmart was going to charge me about $27 in shipping.  That didn’t make sense: all of the items in the cart were SYW Max eligible (that’s the Sears/Kmart free shipping plan, which I belong to).  I tried to return to the shopping cart page to see what was wrong and got stuck in hourglass land…  That is, the screen showed an indicator that it was refreshing, but the page never seemed to load.  I tried other browsers.  No luck.

Finally, I found that I just had to wait about 10 minutes until the page finally loaded.  I tried removing one of the items in my cart to see if that would fix the shipping cost issue.  I waited another 10 minutes for the page to refresh.  No luck.  I removed another item.  Waited…  And, another item.  Waited…  After what seemed an eternity, the shipping fees finally reset to zero.  Yay!

Trying coupons again

I thought that maybe whatever was wrong with my free shipping settings had also caused problems with my coupons.  So, I clicked the link to Apply my Shop Your Way coupons.  I unloaded the 15% back in points coupon and then reloaded it.  And… the shipping fees returned.  That was not what I wanted.

I clicked the Apply my Shop Your Way coupons link again.  This time I noticed that I had loaded a coupon to get a discount on Shop Your Way Max Shipping.  Aha! Maybe I was inadvertently buying another year’s subscription?  I unloaded that coupon.  Success: the shipping fees went away again.

Then, I tried one more time with the 15% back in points coupon.  This time it worked!

I went back and added one of the items that I had previously removed and to my relief I found that shipping was still free and my 15% coupon still applied.  Then, I decided that I had pushed my luck too far.  So, rather than try to add the remaining items, I went ahead and checked out.

I think that I clicked through from Discover Deals again before the final checkout.  I hope I did.  A lot of time had gone by between the initial click through and final checkout and so it would have been easy for Discover & Kmart to lose the tracking info in the process.  Hopefully I was careful (I usually am).

A small points profit

It appears that the 15% points bonus coupon had a $50 limit (even though the details said that the limit was $150).  Overall I earned $50 (about 8.3%) more in points than I paid, pre-tax:

rolling points

I’ll take it.

Math time (or, “Maths” time for those from the UK)

Here are the rewards I can expect:

  • 5% from Discover It card for current 5% category bonus
  • 5% from Discover Deals for clicking through the portal to reload gift cards
  • 5% from Discover Deals for clicking through the portal to buy 100% back in points items
  • 15% from Discover after 12 months of the Double Cash Back promotion

Total expected Discover Cash Back rewards: 30%.  On $600 spend, that’s about $180!  Plus, as you can see above, I was able to use a coupon to earn $50 extra in points.  Later, when I click through the Discover Deals (or any other) portal again to use the SYW points I earned to buy stuff I need, I’ll earn even more rewards.

Some may point out that the value of the process appears to be diminished a bit by the application of sales tax to this order.  That’s not the case, though.  When I actually use my SYW points later, I won’t be charged sales tax.  So, this was, in effect, a way to pre-pay sales tax.  Please see, Roll gift cards into points for triple rewards, for more details.

What about the junk great stuff I bought?

I expect that the items I bought will be handled in a number of ways:

  1. I may use one or two of the items
  2. I may sell some at a yard sale
  3. I may gift some (some of these can make great stocking stuffers)
  4. I will probably donate many of the items to the Salvation Army or to a similar organization for resale

How will I use those points?

Unfortunately, SYW points can’t be used to buy gift cards so there’s no easy way to turn them into cash.  The best use for them is to buy things that you actually want or need.  So, don’t do these tricks unless you know you can spend the points at Sears, Kmart, Lands End, etc.

In my case, I’m ignoring my own advice.  I don’t have a concrete plan for using the points, but here’s my general approach:

  1. Whenever I have to buy anything, I’ll check to see if I can buy it with SYW points.
  2. I’ll regularly look for ways to liquidate or extend the life of points (and I’ll report those options on this blog, if applicable).
  3. As a last resort, I’ll use points to buy and sell items.  Most likely I won’t get all of my money back, but if I get something like 90% to the dollar, I’ll consider it a win.

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 »



    • They still sell stuff within Sears stores and still accept SYW points and Sears gift cards online. One big change is that Lands End gift cards no longer work at Sears or Kmart.

  1. As long as Lands End is participating in the SYW program, I’ll happily do this sort of thing. Their clothes are very nice and reasonably priced, and they have great clearance sales in store. So, if I don’t end up needing anything from Sears or Kmart, I know I can always get school clothes for the kids and get good value from the points.

  2. I find it more useful to split my transactions to more fully use my coupons. you can get your points value vs cost differential much higher that way, in my experience.

  3. You can always try and roll your points until you have something you want to get. Yesterday, I bought over $300 in Kmart stuff from the deal but used $64 in expiring sywr as well. It doesn’t always work, but it’s a way to extend the life of your points until you have something you want to buy.

    • That’s true, but its risky. When I’ve rolled points in the past, I sometimes didn’t get the expected number of points. And, in that case, support wasn’t willing to help.

      • I value SYWR points @25% less then Sears gift cards. Most of the merchandise @ Sears/Kmart cost 30% more then @ Amazon, Walmart, Costco, Restaurant Depot. The only exceptions are some appliances and if you live by a huge Kmart, like in LA area (I don’t), then their sales.With gift cards I can buy Amazon, BP and even Visa gift cards (with a fee). Also, their points expire, often before you need these big appliances. So, I would not do what you did unless i would have a lot of extra Sears gift cards that I bought at a deep discount. On another side rolling points is pure profit. And if it does not work (it did for me numerous times) you can always cancel the order.

        • I was told that you aren’t allowed to buy 3rd party gift cards with Sears gc. How were you able to do that?

        • All Sears stores I tried allowed it. Most Kmart registers hard coded against it, but some still allow. Then its up to a cashier. Additional bonus that with any $50 transaction kmart register print 30 cents off coupon on Speedway. They sell BP cards, but print a coupon for Speedway 🙂

        • What area do you live in? I’ve never heard of Speedway. The Kmart near me used to give coupons toward Sunoco but stopped that a while ago.

    • Did you check how many points were on the final checkout screen? I’m 99% sure you received $64 less than you are expecting. That means that you completely wasted those expiring points. A couple of weeks ago I used only about $2 of points toward one of these types of deals and paid the rest with gift cards. I completely wasted those $2 as my earned points decreased by $2. I will never make that mistake again.

  4. Miler,

    This is so darn convoluted, you got to love it. This is right up there with the old buy Walmart gift card with an ebay gift card bought at Office Max, etc……

  5. So you can get SYW points to buy Sears tires? I assume you like this deal rather than the increased portal % offers?

  6. I hate dealing with Sears/Kmart from past horrors, but against my better judgement, I gave it a shot yesterday after reading your great post. I went through a lesser but similar version of your trials and tribulations, got about $200 worth of items in my cart finally after a good 30-45 minutes, checked out, and got an email notifying me of my order, and saying I’d get another email when it shipped. Then a few hours later I got another email stating I had canceled my order (not!). Called, wasted another 15 minutes of my life, and they said all 7 items I ordered were now out of stock and so they canceled my order. Greg- your detailed breakdown of how to profit from these deals is fantastic and you are a saint for having the patience and desire to fight through the gross incompetence that is the Sears Holdings corporate entity.
    But this was the straw that broke the camels back for me- I’m done with these bozos!!!
    So hopefully it will now a tiny little bit easier for the rest of you still playing the game!

    • Even though it was frustrating, you may have just accidentally hit a minor jackpot:
      1. You might still get portal rewards
      2. Even though they say that they’ll refund to the original form of payment, they sometimes send checks in these situations.

      • 1. In my experience, 95% of the time portal rewards will be taken back after Kmart/Sears order is canceled for any reason. 2. Out of my 3 recent returns 2 came back as a new gift card (one I had to contact them 3 times to receive) and one was credited to a credit card that I used for a partial payment for the order.

      • I paid with a Sears gift card. The order amount was deducted and has not yet been added back. I hope I do get portal CB anyway, but ‘ll probably have to waste even more time trying to get these morons to credit back the order charge to my gift card!

        • In the past when my orders were cancelled and I used a Sears gc I was always given a new gc. They never credit back the old one. A couple of times I did have to complain multiple times before I received it.

        • Whew, new gift card for amount of order showed up in mail today. Here is hoping a check and portal CB comes through as well!

  7. The title of the article is misleading. Rolling points would have been if you used your SYW points to pay for the items and in turn received your points back (plus possibly more). You still got a really good deal but it’s not rolling points.

  8. Great post! As someone who’s done a lot of business with Sears, this is the kind of thing that eventually starts to wear you down (coupons not working, unexpected behavior, etc.)

    This was much more lucrative when actual rolling points existed, at this point in time, it’s harder to justify without the rolling of points…

  9. Speaking of Sears, Greg, I fear they have recently changed their policy regarding shopping portal payouts for purchasing and reloading Sears gift cards. Are you aware of any changes? Experienced claw backs?

    In the last three days I have had 1000’s of Southwest and American points clawed back from my wife, my daughter, and my accounts. All purchases were made through shopping portal, some were for new Sears GCs while most were reloads of GC’s. Purchases were made with CC’s in the same name as the shopping portal name. I always keep a printout from shopping portal the day of a purchase and on all the T&C explicitly state GC purchases qualify for points. Proper online shopping protocol was used.

    GC purchases/reloads prior to 5/2 have not been clawed back. Purchase/reloads on 5/22 -5/31 have been clawed back. I have several more purchase reloads since 5/31 which have posted to accounts but I feel the impending doom.

    Any thoughts?

    • I just had this same thing happen to me. 4k points for one gift card I purchased in early May were pulled from my WN account. I just sent the Rapid Rewards portal an email to find out why but haven’t heard anything back yet. It specifically says Gift Cards should receive points so I’m not sure what the issue would be.

      • Matt, if you don’t mind revealing, was your purchase 1) for new card or a reload? 2) for plastic card or electronic? I’m trying to see if there is any pattern. Of my clawed back orders so far, all have been for new plastic or reload on plastic. Thanks

        • Reload on plastic. Been doing that for awhile with no issues.

          Just noticed the $1k I tried to reload like 2 weeks ago isn’t tracking in the portal either, even though the other purchases I made that day are.

        • Got a response from Rapid Rewards:

          “After looking into your case and account I have confirmed that you have a reversals for your Sears.com transaction. Reversals occur after posting reward to your account and then the merchant audits transactions for the account. Reversals happen when the merchant discovers the use of promotional coupons not listed on the shopping site when making a purchase, returns on a product or service or if the member has made alterations to the purchase. This can also happen when a product was returned and re-purchased in the store, or when any alterations to the transaction have been made in store, such as finding a lower priced item and receiving the difference. ”

          They asked me to upload my receipt “In order to diagnose the proper reason for this reversal”.

          Based on their potential reasons for reversal, I can’t see any valid reason. I didn’t use any codes and gift cards can’t be returned.

        • Thanks Matt. I’m in the same boat and I too have submitted a claim with Rapid Rewards and aadvantage eShopping, both Cartera, but have received no response yet.

        • Just noticed I had AA miles clawed back from my account (and the AA portal) for 3 legit purchases at Sears around the same date (May 18th). Not sure what’s going on.

        • By “legit” do you mean purchases that did not involve Sears gift card/reload? I received the same form letter today from Cartera regarding my Rapid a Rewards account. I will upload requested documents tonight.

        • Thanks for FT link. Overall scenario looks pretty bleak. I believe this fantastic avenue will close for good. I sure hope I’m wrong.

    • This is the first I’ve heard of that. I’d encourage you to contact the portal for support like Matt did. The terms for Sears explicitly allow gift card purchases: “Eligible for rewards on purchase of gift cards effective from and after June 1, 2014.”
      Please let us know what happens

  10. How quickly do SYW points post from Kmart? Loaded up on free stuff from Kmart today and don’t see anything in my SYW account. Email confirmation says the correct amount but nothing is showing up in account yet, figure there is a lag but wonder when I should worry about giving them a call.

    • I should add that when I go to Kmart.com the order detail says 0 points earned. But email receipt says 204910 pending points which is what I saw during checkout

    • The points usually post pretty quickly for me, but I’m not sure what the trigger is. Certainly by the time you get the email saying that they’re shipping your order, the points should be in your account.

  11. When using the Discover portal on the subsequent transactions (i.e: paying with sears gift cards, or SYW points), are you actually getting the CB ?

    Thinking it might be safer to go though upromise for 5%… but of course then you loose out on the Discover IT doubling promo.

  12. Greg, do you find that you have to use a discover card for the purchase in order to get credit through Discover Deals?

  13. How quickly do discover deals rewards points typically post? I haven’t seen any hit my account yet for the GC purchase, purchase of stuff with GC or with points. Transactions are about a week old so probably way to early to be worrying. Plus got one email saying I earned points for using discover deals but nothing is in my account. Not sure if it was clawed back or just hasn’t hit. Also not sure why I only got one email when made multiple purchases.

    • Usually the email comes within a few days, but may take as long as a few weeks. The cash back isn’t actually credited to your account until the next statement close.

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