Non-Citizen of Canada entry to US via border
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Accepted answer
As Long as he holds a valid passport with a US visa in it, like you state, there are no out of routine things expected on this border crossing.
Land or Air don't matter if the documentation is all in order.
He can go back and forth via airports without issues.
Then he can also go via the land borders without any issues.
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Source: stackoverflow.com
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