Sorry I should have clarified, she isn't or wasn't working illegally while she was visiting Canada. She was working for her US based employed remotely via the phone and computer and was able to stay for weeks and a few months at a time, all legally.
I think where the confusion from THEIR perspective is, what will happen when they start to live together full time. As a visitor to Canada, you just can't stay in Canada without starting a process at some point and going through the process. You can only stay for so long before you legally have to leave.
I have cautioned him on making sure they follow everything because of the risk of ever not having the ability for her to come back in the small chance something happens.
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