One savvy shopper spotted a glitch in Loblaws’ brand-new PC Points promotion tied to their MasterCard. Every $1.99 bag of President’s Choice Decadent Chocolate Chip Cookies earned 1,000 points that could be flipped across programs into five times their value at Sears.
For three wild weeks he hit every store, clearing shelves and backrooms until 1,400 bags filled his car and home. He sold most cookies for a dollar each to coworkers, then converted the resulting 1.4 million points through Petro-Canada into $7,000 worth of Sears vouchers, spending only $1,400 net. Petro-Canada panicked, killed the conversion pipeline for everyone overnight.
Canadian Redditor exploited cookie promotion, bought 1,400 bags, flipped points chain for $7,000 Sears vouchers.
Discovering an unintended loophole in a loyalty program and riding it until the wheels fall off? That’s practically a national sport. What our cookie conqueror did is textbook arbitrage: buying low in one market (cookies + points) and instantly flipping the value in another (Sears gift cards worth 5× more). It’s brilliant, it’s legal, and companies absolutely hate it when customers read the fine print better than they do.
On the other side of the table, retailers argue these promotions are loss-leaders meant to build loyalty, not fund someone’s Christmas shopping for the next decade.
When one person (or a handful) extracts outsized value, the company either eats the loss or shuts the party down for everyone, exactly what happened when Petro Canada killed the Sears conversion overnight.
This kind of “rewards gaming” isn’t new. A famous U.S. example involved the Mint’s free-shipping coin orders that let people rack up credit-card points on actual legal tender. The loophole was eventually closed, but not before miles addicts took the Treasury for a very polite ride.
Back home in Canada, the early 2000s were basically the Wild West of points hacking. Air Miles glitches, SDM 20x days stacked with gift-card churns, and yes, multi-step conversions like PC → Petro → Sears were the stuff of underground forum legend.
Most people just wanted a free toaster or a tank of gas; our cookie master saw the same rules and thought, “Why stop at one toaster when I can have the whole appliance section?”
What makes these stories so delicious is the David-vs-Goliath vibe. Giant corporations write the terms, set the traps, and then act shocked when one regular human treats the fine print like gospel and walks away with the jackpot.
Petro Canada didn’t shut the door because they were mad at cookies, they shut it because someone finally proved the house doesn’t always win. And somewhere in a boardroom, a marketing manager is still having nightmares about 1,400 bags marching out the door.
According to the Forter Fraud Index, loyalty program fraud has risen by 89%, with 72% of loyalty managers reporting they’ve experienced such abuse, highlighting the escalating financial strain on issuers from unintended exploits.
Amit Bachbut, a director of growth marketing at Yotpo e-commerce, explains the root cause: “A poorly designed program with overly complex rules, confusing earning structures, or unclear terms can inadvertently create loopholes that fraudsters can exploit.” In this cookie saga, those overlooked gaps baked in the perfect recipe for one person’s sweet victory.
The cleanest takeaway? Promotions should be stress-tested for “what if one guy really commits?” Because when the terms say you can do something, someone out there absolutely will. 1,400 times, if necessary.
Let’s dive into the reactions from Reddit:
Some people jokingly blame OP for personally destroying Sears with the cookie arbitrage.
![[Reddit User] − And people wonder why Sears went out of business. It's all this guy's fault! LOL. JK.](https://dailyhighlight.com/wp-content/uploads/2025/12/wp-editor-1765008962837-2.webp "Man Buys 1400 Cookie Bags And Turns $1400 Into $7000 While Breaking Reward System")
Others compare OP’s cookie scheme to other famous reward-point or arbitrage hacks.
Some people say this story is fun but doesn’t really belong in malicious compliance.
At the end of the day, one Canadian with a sweet tooth and a spreadsheet turned a cookie promo into a $5,600 profit and accidentally helped end an era of easy points conversions. Was he a chaotic hero living the Y2K dream, or just the guy who ruined it for the rest of us?
Would you have stopped at 50 bags… or gone full 1,400 and risked the wrath of Petro Canada? Drop your verdict and your own best loophole story in the comments!
