Upvote:5
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
Upvote:10
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.