Immigration law questions? Ask an immigration lawyer.
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I cannot give tax advice, but as long as you do not engage in tax fraud or are convicted of a crime, it should not negatively effect you keeping and maintaining TN status nor should it negatively impact you getting a green card. Similarly, bankruptcy would not normally negatively impact either.
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Unfortunately, as that is not an immigration question and we have a specific category for tax issues, I am prohibited by the rules of this site from answering that. You'll need to discuss that issue with a tax expert. I'm sorry about that, but this is not something over which I have any control.
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My apologies for posting a response here. Somehow, this question ended up on my question list. Please ignore any request or communications from me. You are working with Guillermo on this question. He will continue to do so.