Canadian citizen entering the US from Europe (Worried about entry being denied)

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...don't want it to look like I'm going to be working remotely in the US...

You're right to be concerned about that. I don't suppose that there is much documentation that could counter that concern, unless possibly a bank statement showing enough money to live on for 5 or 6 months without working.

Does Border Control keep a record of interactions...?

Yes. They might not have recorded it, but you should assume that they did. They admitted you afterward, so they didn't find that you were deceptive to the point of being inadmissible, but you should be careful, as the record (if it exists) could raise suspicions during subsequent interviews.

Therefore I don't have a stamp in any passport that shows the date I left the US. Should my airline ticket and proof of boarding be enough or is there something else I can bring?

You can. There's a real possibility that they did not record your exit because you used your Portuguese passport to check in for your departure flight. (That is not illegal, it's just a possible administrative headache.) You can try checking your records at the I-94 site; if the departure is there then you know you don't need to worry. If it isn't there, you can bring your boarding passes and perhaps a receipt or any other evidence showing your presence in Portugal shortly after your arrival.

I suppose that the last point is likely to be the least of your worries, however. The possibility that you would teach remotely while in the US would be more likely to lead to your being turned away.

Some people may advise you of potential problems from staying for 5 months after claiming a 40-day visit. The UK is notorious for taking a dim view of such circumstances, but I haven't heard of this being a problem with US CBP. This is especially likely to be true during the current public health crisis. The policy of giving all B-1 and B-2 visitors six months is precisely to reduce the administrative burden of having to process extension-of-stay applications from people when their plans change. (Canadian citizens who enter without a visa are nonetheless categorized using the same immigration categories, so a Canadian "visitor for pleasure" is still in B-2 status even though there is no B-2 visa.)

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