Fraud, Embezzlement, Bad Checks Question regarding the legality of employee discount loophole

My question involves criminal law for the state of: Oregon

Alright, so I work at a large retail company and my employee discount is a blanket X% on most items. It is explicitly stated in the employee discount policy that we can use this X% discount to purchase gift cards for ourselves, friends, or family. Pretty good deal, huh? What I realized the other day though, is that you can use gift cards to pay for gift cards.

Let's say this discount is 50% off. That would mean I could buy a $200 gift card for $100, and save $100. Again, this is a completely legit use of the employee discount. However, I could also buy a $100 gift card for $50, and then use that $100 gift card to pay for the $200 card. In this case, I'd be saving $150 instead of $100. At a certain point, the difference between gift card amount increments becomes smaller than the difference between the cost of the gift cards with the discount, and I can pretty much get an infinite amount of multi-hundred-dollar gift cards for just a few bucks.

I've tried this with a small amount already and it worked, my item shipped. It's been about two weeks and no contact from HR or any sign that the company has noticed. This is all automated through their website, and the website allows me to do everything above. Clearly this is a loophole in the discount policy, and there aren't any oversights in their website to prevent employees from exploiting the loophole. I'm aware that if the company notices, I will most likely be fired. However, would the company have any grounds to take legal action against me for exploiting the loophole? It's highly unethical, but doesn't go against the discount policy and I'm not technically deceiving anyone to make a profit.

Thanks for your help!
Additionally, you would not get unemployment and despite what I'm sure you read on the internet, your employer would be free to tell prospective employers exactly what you did to get fired.
You may be right about a legal, exploitable loophole. Since we don't have access to any employee handbook or company policy, we can't comment on what might be contained therein which might be applicable. Nor can we say that the company won't file a lawsuit, even in small claims, to try to enforce a provision of law as applicable in this situation. We don't know the companies and personalities involved.

Some say it is far more costly to be caught stealing a hundred dollars than a million. Taking advantage of a policy you've tried once might be considered a fluke. Consider the cost if you're terminated for engaging in this practice, especially as you may need time to find another opportunity and may not have income as well as what is pointed out above when you're hoping to land a solid, quality opportunity.
If the OP initially spends $50, then by the 20th iteration the OP would have over $52 million in gift cards...perhaps it is ;)
To be clear, I'm being facetious.
Either way you've been watching Superman 3 one too many times. ;)
Either way you've been watching Superman 3 one too many times. ;)
Honestly, I don't ever recall seeing it. I was thinking more about what I was taught by my grandmother when I was very young. Doubling pennies on spaces on a chess board...