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Is it worth rounding up at checkout?
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That's pretty much how it works. I don't know if it's really a should/shouldn't conversation per se. Money is still getting donated to the needy, it's just also kind of undercutting what the company should be doing in terms of taxes and stuff. And some people just can't get themselves to make the time to donate directly.
That said, 100%, if you can get yourself to make the time to donate directly to a cause, that is absolutely undeniably better than letting the company do the roundup thing and you should totally do that instead.