A legal riddle: what's the difference between avoiding and evading a reporting requirement?

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For years, I’ve held what I think is the mainstream view in the travel hacking community:

But I recently ran into a situation that has me somewhat baffled.

I want to comply with reporting requirements but Walmart won’t let me

As many readers know, Walmart recently started requiring cashiers to input data from a government ID for money order purchases over $1,000. This slowed down the process of liquidating high-denomination Visa debit cards, but since my stores only allow one transaction with up to 4 debit card swipes, it wasn’t the end of the world, just adding 2-3 minutes per day to my liquidation routine.

The other day, I ran into a different problem: after inputting all the information from my ID, the computer simply dumped the cashier back into her main screen, without allowing the purchase to proceed. No explanation was given, so I have no idea if this was a one-time glitch or if my information has been flagged for some reason.

However, purchases below $1,000 don’t require ID, so I’m still able to liquidate, for example, three $300 Visa debit cards or two $499 Visa debit cards.

Now you can start to see the problem: if a store has a reporting requirement, but does not allow you to fulfill the reporting requirement, does it constitute structuring to instead make transactions that don’t trigger the reporting requirement? In other words, if I’m avoiding triggering, rather than evading complying with, the reporting requirement?

You can imagine more clear-cut cases. Since even nearby Walmart stores can have vastly different store policies, you might have access to one store that allows 4 debit swipes per day, one that allows 2, and one that only allows 1 swipe. If you want to liquidate a stack of $500 debit cards, you could visit each store once per day, triggering the reporting requirement at two of the stores ($2,000 and $1,000 transactions) and not triggering it once (the $500 transaction). There would clearly be no problem in this situation since you’re in full compliance with each store’s policy on transaction limits and company policy on reporting requirements. I actually used to do something like this fairly regularly.

You can also imagine clear-cut cases of violations. If a store has a policy of only allowing one swipe per day, you might visit the same store once on your way to work to liquidate one $500 card, and the same store on your way home to liquidate another. In this case you’d obviously be exhibiting a pattern of behavior deliberately intended to evade both the store’s one-swipe policy and the company’s reporting requirements. Don’t do that.

But my case seems to fall right in between those two bright lines. If I’m in full compliance with store policy (using only 2 or 3 of my four allowed swipes), and company policy (reporting requirements are only triggered for transactions above $1,000), then is it legitimate or illegitimate to keep my transactions below the reporting requirement, with which I am more than happy to comply? In other words, I’m not trying to evade the reporting requirement, I’m trying to avoid triggering what is, for all I know, simply a bug in their reporting software.

Conclusion

Vinh at Miles per Day mused the other day that 2019 will see more people questioning their ethical lines and delving deeper into gray zones, and I suppose this is a version of that. Structuring is a bright line that I have no interest or willingness to cross, and that hasn’t changed. Rather, I’ve run into a new situation and I simply don’t know which side of that bright line it falls on.

All travel hackers are amateur lawyers, so I trust you’ll sound off in the comments.