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hurting me is their intention so I appreciate the help on the logistics of all of this! I will bring all of this info to my advisor when I file my taxes this year (assuming they go through with it and send me the 1099)

@Confused96 wrote: They stated they will be sending me a w2 as usual and a 1099 just for the training  So that's clearly improper, and it's not taxable to you.  The question is how to not get the IRS on your back while it gets sorted out.   (The problem with a lawyer is it could cost you more than the amount of the dispute.)   Although there may be other opinions, I would not include the 1099 as taxable income.  There are two ways to do this, both of which will likely trigger the IRS to look into it.  a. Enter the 1099 as miscellaneous (other) income, not related to work you did (even though it;s a 1099-NEC).  Then enter a negative amount of miscellaneous income as an offsetting adjustment.  You can e-file this way.  The IRS computer will see that you reported the 1099 as income, so it won't be an immediate red flag, but they will probably ask at some point for an explanation of the negative adjustment. b. Leave the 1099 off your return, file by mail, include a copy of the 1099 and a written letter of explanation.  The. IRS may still ask for information later.   Either way, this is profoundly stupid by the employer.  They don't get any more of a tax deduction for 1099 income than they do for training expenses, it just hurts you. 

When you prepare your tax return you will enter a 1095A into the software, showing the amounts of the tax credit you received.  You must get the 1095A from healthcare.gov. TO FIND A 1095-A with healthcare.gov   How to find your 1095-A online Log in to your account. Under "Your Existing Applications," select your 2025 application — not your 2026 application. Select “Tax Forms." Download all 1095-As. Get screen-by-screen directions, with pictures (PDF, 504 KB).         If you had health insurance from the marketplace, when you applied for the insurance, you gave healthcare.gov an estimate of how much income you would receive in 2025.  They used that amount to calculate how much of the insurance premium would be covered by the tax credit and how much would be your amount to pay.   So...you had some monthly amounts to pay, and the rest of the cost of having that insurance was paid by the government program.   If you ended up making a higher income than you told them you would receive, they re-calculate how much should have been paid by the program and how much should have been paid by you.   And if your own share of the cost should have been more, they get it back on your income tax return.      If you actually had less income, you could even get some of the share you paid back on your tax return.      

Wait to see if the company actually sends you a 1099. If they don't, then you just file your tax return with your W-2 as usual. If they do send a 1099 for money that they did not pay to you, I would not waste time trying to figure out a way to report it on your tax return. That's not really the issue. It's a fraudulent 1099. I would suggest that you see an employment lawyer about it.  

Thanks for the insight and yes I would run the federal both ways for a decision. Where I’m more confused is the state taxes for RI and MA for both of us and how the federal impacts them. Would state filing dictate married separate?  What would be required for my wife in RI as a non-resident and for me in MA as a non-resident?  I’m retired and ky wife and s still working so income predominantly will be in MA. 

I would not agree to pay them anything, especially if you don;t have a written contract.    If they report a 1099-NEC instead of a W-2, the first thing you do is file form SS-8.   This is a request to have the IRS determine your status.  If you have pay stubs showing withholding of taxes, especially SS taxes, you can include that as proof, along with any other information suggested in the instructions. https://www.irs.gov/forms-pubs/about-form-ss-8   You might remind the company about the SS-8 form, and the heavy penalties that companies pay if they are found to have misclassified employees.     As regards to your tax return, that is a little more complicated.  If they withheld social security and medicare tax from your paychecks, it will be almost impossible for them to report your pay on a 1099-NEC and still balance their books.  If that does happen, form 8919 is probably not correct, because it will tax you for half the social security that was already withheld.  I would see an accountant for help (and not a storefront).  Probably you would use a substitute W-2 form instead, but this will also cause an investigation and likely delay any refund.   However, it sounds like they might only want to issue a 1099 for the money paid for the training, as if it was paid to you.  This would also be improper, and would not make any sense.  If you are a regular employee (a common law employee) then the company can deduct your training as a business expense.  If they report it as 1099 compensation, it still is a business expense to them (they don't get a better deduction) but it hurts you, so the only reason to do that is spite.  It would not be taxable to you in that case.  I think your best option in that case would be to file your return by mail, not including the training money.  Instead, print your return and mail it in.  Attach a copy of the 1099 and a written letter of explanation that also says you have filed an SS-8.  (And you will include the 1099 and the explanation as part of your case when you file the SS-8).   It is ultimately unclear to me whether they want to 1099 you for the wages, the training, or everything.  Best to wait until you actually get the documents and then we can talk about how to handle it.  

@Opus 17 wrote: Look up "Advance Fee Scam" on your favorite search engine.  https://en.wikipedia.org/wiki/Advance-fee_scam   Almost certainly a scam. Why would someone you presumably don't know and have never met gift you money, @schultzprojectmanager?

I understand your position, but the problem is you don't own the farm, the trust does and the expenses should be deducted at the trust level.   If your attorney is of the opinion that it is proper for both the trust AND you to file a Schedule F, then why did you even bother posting this scenario on this board?   I'm not going to argue with the manner in which your attorney suggested handling this issue (although I personally wouldn't advise a client in the same manner), but I can't imagine how this won't raise issues with the trust reporting virtually all of the income on its 1041 (from Schedule F) and you reporting only $1 worth of income with a number of expenses thus showing a loss on the Schedule F you would be filing with your 1040.   Good luck.

Thanks again for your feedback after the extensive research. I really appreciate it. The recipient in this case my wife generally uses the original owner's cost basis per IRS guidelines, and the original cost basis for this asset has been moved to 2001 per India Govt Guidelines. Therefore, as stated, with a certificate in hand confirming the asset cost basis as of 2001, we should be good to go and will proceed.

Be extremely careful.  Use some of that money to hire a lawyer before you send any money to anyone.     Look up "Advance Fee Scam" on your favorite search engine.  There are thousands of examples.  Never pay out money to get more money.   The US does not tax large gifts to the recipient.  (There is a report that must be filed for gifts from foreign persons of more than $100,000 but there is no tax owed.)   If the Netherlands or England supposedly taxes this gift, that tax should be paid by the giver before the balance is sent to you, not paid by you before you get the money.     Assuming this is a real gift, gifts are gifts, not contracts.  Once you get the money you can legally keep it all.  If this is a contingent gift (you must do X to get Y) then it is a contract and you should have any contract involving that large an amount of money reviewed by a competent attorney before you agree to anything.  Attorneys also have escrow accounts that can hold the "taxes" so they are paid properly, if they are real.   But it's probably a scam.