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I think people underestimate how many stores used to set prices to avoid pennies. When I was a kid it was frequent. Goose the price so cost + tax rounded to the nearest nickel. But now everything is 23.99 or sometimes 23.95, and they use the pennies place to denote clearance items. Like 19.94 or 3.98.

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There’s a reason for this. Prices that force cashiers to make change force them to run the transaction through the cash register so it is recorded, and the amount in the register can be checked at the end of a day or shift to detect theft. If prices are round numbers, such as $1, the cashier can pocket the payment.

I don't get it. Why couldn't a cashier pocket $1.99?

Because they were handed $2 and have to get the change out of the register.

Ok, but if the cashier is stealing they could just have change in their pocket?

I'm skeptical that preventing theft is the reason for these prices rather than the psychological trick of looking cheaper.

Now that you mention it, there’s quite a lot of overlap between family owned and this pricing to my recollection. If your wife is stealing from the till that’s very different from some high school guy you hired.

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