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I live in Canada and will travel to USA tomorrow for non-essential purposes. I return on Sunday. On Monday I start a new remote job in Canada.

I want to take both my personal and work laptop, because what if I can't fly on Sunday for whatever reason? (e.g. if my COVID test comes back positive and they don't let me board). I can't miss my first day at work.

Will the USA border agent think this is strange? E.g. they may think that I plan to work there and deny the entry? I can show them my return ticket, but is this enough?

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    You say you start a new job on Monday. So what is this "work laptop"? Did your new company give you a laptop before you start, or do you have two laptops that are yours and which you label "work" and "not work"? Sep 22 at 14:16
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    Possible duplicate of: travel.stackexchange.com/questions/12771/…. The two laptops are a distraction in this case. The real question is purely around working in the US, not the lapops.
    – JonathanReez
    Sep 22 at 22:52
  • @DJClayworth the company gave me a laptop before starting. It's a remote job Sep 22 at 23:49
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    Also if you "can't miss your first day at work" why are you taking the risk of doing so by travelling "for non-essential purposes". Sep 23 at 12:48
  • @DJClayworth that's why I took my laptop. I was gonna work from my friend's place. Sep 23 at 19:33
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Not in itself. It is a reasonably normal occurrence for people to take a personal and work laptop. The suspicious part is the duration of the trip which you may have to explain. Which questions get asked are at the discretion of the immigration agent which is unlikely to notice you have two laptops unless you are carrying two laptop bags. The explanation you gave here in your question is quite reasonable during these times.

Security screening is done by different staff. They see your belongings plus passports and boarding pass but are not trying to check if your belongings match your trip. Laptops are screened separately and so security will see that you have two laptops. They often target those for additional screening or scan for some reason but I've never heard them voice any concern about this.

Pre-covid times, I crossed between the US and Canada multiple times per year, frequently for a few days and invariably got more questions from immigration about short trips than longer ones. Only once did immigration question why I was carrying substantial bulk relative to the length of my trip, only on the way back to Canada. That time, I had large work gear with me and needed an extra suitcase that was mostly empty, so I was sent to a secondary inspection where they passed all my baggage through X-ray again before letting me continue on my way home.

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  • Thank you! It is a short trip indeed. Sep 22 at 4:19
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    1. Really, is a 4-day trip (Wed-Sun) to a neighboring country suspiciously short? 2. "I've heard them voice any concern about this" -- missing a "not" or "never"?
    – nanoman
    Sep 22 at 11:55
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    People do day trips from Canada to the US all the time. Sep 22 at 14:18
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    Yes, day trips are common and, between the US and Canada in particular. I have done many and know people who did it almost weekly for years. It is clear that shorter trips get more questions when flying in. Driving across the border, I have not noticed any differences but nearly all my land-crossing were short trips. My guess is that there is probably a statistical correlation between short trips and illegal cross-border activity.
    – Itai
    Sep 22 at 16:17
  • @nanoman - Sorry, corrected the missing world. Border agents have to decide who to ask questions from and when to ask more, so if statistically illegal travel involves shorter trips, then shorter trips become more suspicious. Single travelers also are generally more suspicious and conversely when I travel with family tend to be waived through with virtually no question other than destination.
    – Itai
    Sep 22 at 16:22
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I lost count how many times I crossed the USA - Canada border first as a Canadian resident on a Hungarian passport with a ten year B1/B2 visa and then on a Canadian passport -- always with at least two laptops. (Sometimes three.) Never a problem. Other countries too. I never had an agent ask me why I have a pile of laptops :)

Note attending meetings is a perfectly fine B1 reason and that very well might need a work laptop vs personal laptop. https://travel.state.gov/content/travel/en/us-visas/business.html

Examples of temporary business include:

Attending business meetings or consultations

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