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I have an upcoming vacation for a couple of days in Canada (as a leg of a longer trip in the US [I am a US citizen]). I'd like to bring my company-owned laptop so I can check my email while I'm there. My company has provided me with a letter for customs with a bunch of legalese explaining that it's OK for me to bring the laptop into the country.

Do I need to notify the customs officials that I have the laptop, or is the letter only to be presented if it comes up?

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No you do not have to do anything unless asked (and that is unlikely). A sizeable fraction of people traveling will have notebook computers with them, owned by themselves or their companies. Nobody typically pays much attention to a machine that's obviously not brand new in the box.

However, keep in mind that officials on both sides of the border can ask for passwords and sift through any of your electronic devices if they feel like it.

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    Officials on the US side of the border can ask a US citizen for their password but can’t do anything if you say “no”.
    – JonathanReez
    Commented Aug 25, 2022 at 22:03
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    @JonathanReez: They might not be able to require that you reveal your password, but they have nearly unlimited power to make your life more difficult in other ways. Commented Aug 25, 2022 at 22:39
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    @JonathanReez they can. They can confiscate the device under "suspicion of being related to a criminal organisation or terrorism" or something like that until they either manage to break in or you hand over your credentials. And they can basically do the same to you plus "obstruction of an official investigation" which is a federal crime. TSA and DHS have near unlimited powers like that, which is why many non-US companies now won't allow their employees to take ANY company owned devices through US customs.
    – jwenting
    Commented Aug 26, 2022 at 10:09
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    @jwenting Exactly that. Were I work nobody travels to the USA with a company laptop or phone. The US based offices have loaner equipment available for visitors from outside USA. Due to industry regulations and GDPR compliance our employees are not allowed to give border-control access to the equipment and can potentially be confronted with a lot of hassle, detention or being refused entry. We just don't want to expose them to that.
    – Tonny
    Commented Aug 26, 2022 at 10:49
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    @JonathanReez your comment and the following replies are a nice example of US freedom in theory vs US freedom in practice Commented Aug 26, 2022 at 19:50

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