I live 30 mins north of Coutts so I cross the border at least 5x/month (beer,cheese,cherry coke and other essentials). As I understand it, and as I have experienced, it all comes down to the border guard. If you exceed your exemption then they can technically take the entire exemption away and you would be paying on the entire purchase, I have been warned about this on 2 occasions but it has never happened to me. I have found that being polite, upfront and honest has saved me hundreds of dollars on taxes and duties, in a lot of ways it is probably more important to the border guard than tax laws
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