Originally Posted by
UND_jesse
D Never travel with both.
Exactly. Most border guards don't know the rules anyway and will detain you for having 2 passports.
As far as the Cuba thing - I was looking for more of a legal loophole than a "just bring the Canadian passport". Seems like you legally couldn't go there once you claim US citizenship. Just wondering if there were exceptions for people who fly mail or cargo there.