Cross US border with two laptops
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Generally not more than anyone else. Traveling with 2 laptops is certainly an exception but most will not even notice. You may get an additional question or not but that depends on the officer in question. Screening is quite streamlined in most airports and you will have to put two laptops in two bins as they go through the x-ray. The usually ask to inspect the luggage if something looks suspicious but do not keep perfectly track of what belongs to who since there is a different screener at the x-ray than at the body-scanner or metal detectors.
When something is considered suspicious or gets selected by random inspection, they usually ask to whom the item belongs and ask you to watch while the inspect. Most times, there are no questions. If there is one, it is up to you to state the truth simply as possible. Remember, security is different than customs, as far as I know they do not question value and allowance, they are mostly concerned if it is a security threat.
When passing through customs going back to Canada, if you are selected at random for inspection, it is possible they will ask why you have two laptops. If they look used, then you will be good to go but if you want to play safe, have the receipt with you (at least for yours) showing that you paid Canadian taxes on it and the business one could have the name of your company or an inventory label on it.
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