Roll gift cards into points for triple rewards

33 has long been special in that it’s one of the few online merchants that explicitly allows earning portal rewards when buying gift cards.  The terms & conditions listed under in many portals say, in part:

Eligible for rewards on purchase of gift cards effective from and after June 1, 2014.

So, when portals offer increased rates at, some people like to earn miles or cash back by buying gift cards.  To get an idea of how often portals offer increased rates at Sears, take a look at a section of the “best history” chart for Sears, from Cash Back Monitor (click the chart for full details):

Roll gift cards into points

As you can see above, it is often possible to earn 8 to 10 miles per dollar at Sears.  Since gift card purchases are eligible, it is actually easy to average 16 to 20 miles per dollar by “double dipping”– go through a portal once to buy a gift card and then a second time to buy merchandise and pay with the gift card.

24 to 30 miles per dollar and free stuff too

One way to earn triple portal rewards is to roll your gift card value into Sears’ Shop Your Way Rewards (SYWR) points, as follows:

  1. Go through a portal to buy Sears’ gift cards
  2. Go through a portal and use gift cards to buy items that earn 100% back in SYWR points.
  3. Go through a portal a third time to use SYWR points to buy what you really want.

Earlier this week, certain portable rechargeable batteries were available from Sears with 100% back in points (details here).  I clicked through the Discover Deals portal which is currently offering 5% cash back at Sears (and, that 5% will eventually be doubled to 10% thanks to Discover’s current Double Cash Back promotion) and I bought 4 of each item.  And, I paid with Sears gift cards that I had bought last week (actually, I had reloaded an existing gift card with $500 after going through the Discover Deals portal which was offering 10% cash back at the time).

Roll gift cards into points

Roll gift cards into points

The next day, I was able to buy four more of the $14.99 item:

Roll gift cards into points

Sales tax pre-payment

As you can see in the above image of my second day order, I earned slightly more in points than the pre-sales tax price.  However, with sales tax it appears that I lost some value.  $63.56 was deducted from my gift card, but I earned only $60.56 in points.  Not counting the value of the items purchased, that appears to be a $3 loss.  It’s really not a loss, though.  Instead, you can think of it as a sales tax pre-payment.  Later, when you buy something you actually want and use points to pay for it, you won’t have sales tax applied for the portion of the order that is paid for with points.  To demonstrate, I added a $78.01 item to my cart and selected to pay for the entire order with Sears’ Shop Your Way Rewards points.  No sales tax is charged:

Roll gift cards into points

Free Shipping: Shop Your Way MAX

Sometimes Sears offers an easy way to get free shipping with your order (for example, as I write this, they’re currently offering free shipping for orders of just $25 or more).  Otherwise, shipping fees can ruin deals like these.  Other than waiting for Sears’ shipping deals, there are a few options for avoiding shipping fees altogether for many items.  One option is to sign up for the Shop Your Way MAX shipping program.  For $39 per year, you get free 2 day shipping on eligible items (your cart must include items for $10 or more each, or totaling at least $30 worth of eligible items).  And, at the start of each month, you get $3 in points which have to be used by mid-month before they expire.  You also get an extra 5% back in points (up to $50 per year) when you select in-store pickup for eligible items.  If you play it right, the free shipping program can easily pay for itself.

If you buy enough from Sears and Kmart to become an elite member, you may find a coupon in your account that let’s you buy or renew SYW MAX for half price:

Roll gift cards into points

Free Shipping: Store Pickup

Another option for avoiding shipping charges is to select FREE Store Pickup when adding items to your cart.  Unfortunately, availability varies by item and location.

Roll gift cards into points


It is often possible to do better than 100% back in points by applying coupons to your order.  Here are a few ways to find useful coupons:

  1. Follow sites like SlickDeals (click here for an example SlickDeals post showing how to get Sears coupons)
  2. Find coupons on whatever portal you use. Most portals list coupons specific to whichever merchant you plan to click through to.
  3. Watch your email.  Once you enroll in the SYWR program, you’ll get plenty of emails. Some will include useful coupons. Usually you have to click to load to your account.
  4. Log onto your account within and hover the mouse over the “Deals” menu item, then select “Member Coupons”.  For each coupon of interest, select “Load to Account”.


When buying items, you can add coupons to your order on the shopping cart screen.  Click “apply my Shop Your Way coupons” to find coupons loaded to your account and to add them to the order.  Coupons may or may not actually get applied depending upon their specific terms.  For example, many coupons exclude “hot buy” items.

Roll gift cards into points

Occasionally you’ll have to choose between a coupon that offers a cash discount and one that offers extra points back.  For example, you might have to choose between 5% off or 10% extra back in points.  Usually, I recommend saving cash.  However, with some (but not all) 100% back in points offers, saving cash also reduces the amount of points you’ll get back.  In those cases, getting extra points is preferable.

Rolling points into points

Every now and then there will be a 100% back in points deal in which the points “roll”.  This means that you can pay as little as one penny with a credit card or gift card and pay the rest with points and earn 100% back in points.  This can be a terrific way to get free stuff, renew the lifespan of your points (since points have expiration dates), and earn extra portal rewards.  However, I don’t recommend doing this.  When this works, it is not intentional on Sears’ part.  They don’t like it.  And, a few bad things can happen:

  • You may earn fewer points than promised in the checkout screen.  If so, customer support won’t help you.
  • You may have your SYW account closed down and points revoked.
  • I’m sure there are other possible negative outcomes as well.

Again, I don’t recommend rolling points into points.

Problems with SYWR points

Rolling gift card credit into SYWR points can be a great way to increase rewards, but there are significant downsides you should be aware of:

  • Points Expire: Points earned on regular purchases are usually good for a full year, but bonus points from 100% back in points deals often expire within 90 days. If you don’t have a near term plan for spending those points you could lose them entirely.
  • Points can’t be resold:  If you get stuck with Sears gift cards that you can’t use, you can always resell them instead. Use a site like GiftCardWiki to find the best resale rates. You’ll probably get less than 85 cents to the dollar, but that’s much better than nothing.  SYWR points, though, can’t be resold directly.
  • Points can’t be used to buy gift cards: You can’t use points to buy gift cards so there’s no easy way to “upgrade” from points to gift card credit.  Technically, you’re not supposed to be able to buy gift cards with gift cards either, but in-person some cashiers allow it.
  • Points can’t be used to earn more SYWR points: Most of the time, any part of an order that’s paid for with points won’t earn any additional SYWR points.
  • Points can’t be used to buy Marketplace items: Sears lets other merchants sell things through  Often, those items are ridiculously overpriced, but sometimes they can be competitive. Unfortunately, even though you can earn portal rewards when buying these items and you can pay with gift cards, you can’t pay with SYWR points.
  • Points could become worthless if Sears goes under: This is true of gift cards too, but maybe more so. If Sears declares bankruptcy it seems possible that SYWR points could lose all value overnight.
  • Rolling gift card credit into SYWR points isn’t scalable:  Deals offering 100% back in points tend to have strict limits (e.g. limit 4 per customer) and they tend to sell out quickly.  While its likely that one could roll hundreds of dollars worth of gift cards into points each year, I wouldn’t count on doing thousands of dollars worth.
  • Items purchased with points (or with gift cards) are not covered by credit card purchase protections: If you’re counting on your credit card to give you an extended warranty or price protection, you won’t get it if you pay with points or with gift cards.

Wrap up

Sears offers amazing opportunities for earning points, miles, and cash back.  If you get into buying items at 100% back in points, you’ll not only earn rewards, but you’ll also get free stuff that can be used yourself, given as gifts (they sometimes make great stocking stuffers), given to charity, or resold.  At the end of the day, though, you’ll have points that need to be spent at Sears, Kmart, Lands End, etc.  Fortunately, those stores cover a lot of ground: clothes, shoes, toys, tools, appliances, electronics, household supplies, eyeglasses, automotive supplies (e.g. tires), prescription drugs (Kmart), groceries (at Kmart), and much more.

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[…] Sears and Kmart frequently offer deals for 100% back in SYW (Shop Your Way) Rewards.  By clicking through a portal to Sears or Kmart to buy those items, you can earn additional portal rewards.  Plus, often its possible to apply coupons or stack offers so that you’ll earn more in rewards than you paid.  For details about this approach, please see: Roll gift cards into points for triple rewards. […]

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Dale Reardon


You Americans are so lucky with your reward schemes.

I’m an Australian and we have nothing as good as this.

Wish I could earn more AA miles so easily through portals.



I follow slickdeals but I never understand where people find the 100% back offers that get reported there. I never see them in email from SYWR, so do people just happen run across them?


Here’s how I always find them, from the sears/kmart main pages look for the deals section and choose member exclusive deals and you should see the full list of point back deals. Just scroll down looking for the 100% back in points offers.


This might just be me being paranoid but I have had portal issues with tracking Sears/Kmart purchases if I used points to pay for the entire purchase, so I’ve usually taken making sure my card is charged a few cents, seems to make the portal systems happier.

[…] Roll gift cards into points for triple rewards by Frequent Miler. If you’re not familiar with SWYR points, then this post is an absolute must read. Lots of profit to be made here. […]


How long does it take to have the points so I can spend them on what I want. Thanks!


I’ve received them immediately after placing an order.


Sorry for the random question: I seem to be only able to buy GC from GCmall in denominations up to $250. Am I just not doing something right. The added cost is a lot higher than with $500 denominations.


I always knew you were a Sears fan, and now I know why. Triple dipping is awesome, but obviously requires more work, and selling to liquidate. Too bad the secret gift card rack doesn’t take points.
I have read that Sears is a troubled business and one should limit their gift card exposure, because one day they could be worthless.
I would suggest to anyone playing with sears to stay small, cycle your triple dips quickly, and don’t get caught with many cards or points in the end. Likely the deals will become more lucrative, just before the axe drops.


” Likely the deals will become more lucrative, just before the axe drops.” Absolutely! Deals like these here warn me that Sears is way down this road already. How many here remember the “free after rebate” website of about 15 years ago?