Can I resubmit W8-BEN with W9 form?
Since you're a US citizen, submitting W8-BEN was wrong. If you read the form carefully, when you signed it you certified that you are not a US citizen, which is a lie and you knew it. W9 and W8 are mutually exclusive. You're either a US person for tax purposes or you're not, you cannot be both. As a US citizen - you are a US person for tax purposes, whether you have any other citizenship or not, and whether you live in (or have ever been to) the US or not. You do need to file tax returns just like any other US citizen. If you have an aggregate of $10K or more on your bank accounts outside of the US at any given day - you need to file FBAR. FATCA forms may also be applicable, depending on your balances. From foreign banks' perspective you're a US person, with regard to their FATCA obligations. Whether or not you'll be punished is hard to tell. Whether or not you could be punished is easy to tell: you could. You knowingly broke the law by certifying that you're not a US citizen when you were. That is in addition to un-filed tax returns, FBAR, etc etc. The fact that you were born outside of the US and have never lived there is technically irrelevant. Not knowing the law is not a reasonable cause for breaking it. Get a US-licensed tax adviser (EA/CPA licensed in the US) to help you sort it out.
I received a $2,000 bonus... Gross Income is income from whatever source derived, including (but not limited to) “compensation for services, including fees, commissions, fringe benefits, and similar items.”  Adjusted Gross Income is defined as gross income minus adjustments to income.  My question is, must I still report this money on my tax return and if so, how? Yes, and it would be on line 21 of your 1040 with supporting documentation. Are these legal fees deductible as an expense, and where would I list them? Yes, you would aggregate your deductible expenses and place these on your Schedule A. Instructions here. Good Luck. Edit: As Ben Miller pointed out in the comments, the deduction would be placed in either line 23 or 28 depending on the nature of the attorney (investment related or not). With the W8-Ben filed, tax will be withheld at a lower rate. (I would expect 10%). Tax treaty treatment will mean that this witholding will reduce your UK tax even if this payment is not taxable there. This is only effective if you actually pay tax. This is how it works for lotteries and dividends as well. This might be a question better suited for r/askeconomics or just r/economics. Ben Bernanke is an excellent source on the Great Depression, however, and he's very good if you want to understand these crises from an economic point of view. It looks like you can.  Take a look at these articles: http://www.googobits.com/articles/1747-taking-an-itemized-deduction-for-job-expenses.html http://www.bankrate.com/finance/money-guides/business-expenses-that-benefit-you.aspx http://www.hrblock.com/taxes/tax_tips/tax_planning/employment.html But of course, go to the source: http://www.irs.gov/publications/p529/ar02.html#en_US_publink100026912 From publication 529: You can deduct certain expenses as   miscellaneous itemized deductions on   Schedule A (Form 1040 or Form 1040NR).   You can claim the amount of expenses   that is more than 2% of your adjusted   gross income. You figure your   deduction on Schedule A by subtracting   2% of your adjusted gross income from   the total amount of these expenses.   Your adjusted gross income is the   amount on Form 1040, line 38, or Form   1040NR, line 36. I hope that helps.  Happy deducting! Great, thank you very much! I guess I will just do my 7/66 first and then worry about the others (CFP or CFA) later if I really want to get them. I just wanted to make sure I wasn’t doing something I didn’t *really* need to do. According to the W9 instructions you are considered a U.S. person if: According to the following section, it looks like a C corporation may be easier then an LLC: All of this information can be found here: http://www.irs.gov/pub/irs-pdf/fw9.pdf Hope this helps! IRS pub 521 has all the information you need. Expenses reimbursed. If you are reimbursed for your expenses and you   use the cash method of accounting, you can deduct your expenses either   in the year you paid them or in the year you received the   reimbursement. If you use the cash method of accounting, you can   choose to deduct the expenses in the year you are reimbursed even   though you paid the expenses in a different year. See Choosing when to   deduct, next. If you deduct your expenses and you receive the   reimbursement in a later year, you must include the reimbursement in   your income on Form 1040, line 21 This is not unusual. Anybody who moves near the end of the year can have this problem. The 39 week time test also can be an issue that span over 2 tax years. I would take the deduction for the expenses as soon a I could, and then count the income in the later year if they pay me back. IF they do so before April 15th, then I would put them on the same tax form to make things easier. You should not continue contributing, as you're no longer qualified for it. You can keep it, and use the money in it toward the current medical expenses, without a problem. There are specific examples in pub 969.