Thanks for that tip about the adjustment code! I didn't even know I had to indicate why I was changing the basis. How detailed do I need to be with the explanation? Is it enough to just say "RSU vesting date FMV" or do I need to provide more documentation?

Code "B" is all you need on Form 8949 - you don't need to write a detailed explanation. However, I highly recommend keeping documentation that shows the fair market value on the vesting date. This could be your vesting statements, pay stubs showing the RSU income, or a statement from your company's equity portal. If you get audited (which is unlikely but possible), having that documentation ready will make the process much smoother. The IRS mainly wants to ensure you're not double-counting the income (once when it vested and again when you sold), or trying to avoid taxes by artificially increasing your basis.

You should definitely use the Supplemental Information! That's actually the correct data for your tax return. The official 1099-B often shows zero basis because that's what brokerages are required to report to the IRS, but the Supplemental Information shows the actual cost basis you should use. This is a really common issue with RSUs. The brokerage knows you need the adjusted basis information but they can't put it on the official 1099-B form due to IRS reporting requirements. That's why they provide it separately.

I don't qualify as independent under any of those categories unfortunately. I'm 20, unmarried, and don't have kids. What's the professional judgment process? Is that different from the dependency override?

Professional judgment is different from dependency override. While dependency override changes your dependency status completely, professional judgment allows financial aid administrators to adjust your financial aid package based on special circumstances. In your case, you'd still need to file as dependent, but the financial aid office could potentially adjust your Expected Family Contribution based on the fact that you're not actually receiving support from your step-father despite what the FAFSA calculations assume. This might not solve your immediate filing problem, but could help with actual aid amounts if you do manage to submit your FAFSA.

This is good advice. I had a scholarship organization work directly with my school when my dad refused to file taxes. They arranged a temporary funding solution while I worked through the dependency override process.

Thanks for bringing that up! I hadn't considered FATCA at all. My investments are pretty minimal, but I should definitely check if they exceed the threshold. Do you know if the 40% ownership in my small company would trigger any special filing requirements? It's definitely not a passive investment - we actively run the business together.

Your 40% ownership in an active business where you're actually working probably won't trigger PFIC concerns, but it might require you to file Form 8858 (for foreign disregarded entities) or Form 8865 (for foreign partnerships), depending on how your business is structured in Argentina. These forms basically just disclose your ownership interest to the IRS. Since you're actively involved in the business, you would report your income as self-employment income on Schedule C, and you'd need to pay self-employment tax unless there's a totalization agreement between the US and Argentina. The income itself might be excludable via the Foreign Earned Income Exclusion, but the SE tax often still applies.

This is so true! I moved from UK to Massachusetts and was shocked at how complicated everything is. In the UK, most people don't even file taxes - it's all done automatically through your employer. Here I had to learn about federal, state AND city taxes in some places.

Thank you so much for this info! Do you know if there's any way to get the penalties reduced if it really was due to an employer error with the withholding? My husband asked HR to withhold additional money from each check and they apparently never set it up correctly.

You might be able to request penalty abatement, especially if this is your first time having an issue with taxes. The IRS has what's called "First Time Penalty Abatement" which can waive penalties if you haven't had any significant penalties in the past three tax years and have filed all required returns and paid (or arranged to pay) any tax due. For the employer error specifically, that's unfortunately common and usually doesn't qualify for special treatment on its own since ultimately it's the taxpayer's responsibility to verify proper withholding. However, you could request a letter from HR acknowledging their mistake, which might help support your case for penalty abatement. I'd recommend filing on time, setting up a payment plan, and then separately requesting the penalty abatement afterward.

An extension gives you more time to file your tax return (until October 15th), but it doesn't give you more time to pay what you owe. The payment is still due by the original tax deadline (usually April 15th). If you file an extension but don't pay by the original deadline, you'll still face failure-to-pay penalties and interest on the unpaid amount. However, you'll avoid the much larger failure-to-file penalties, so it's still better than not filing at all.

Oh that makes sense! I thought it gave you extra time for both. Thanks for explaining that - definitely good to know!

This is really important! We had this exact issue when selling our farm - the equipment was going to trigger additional withholding until our accountant separated it out properly. Does this vary by state? We're in Minnesota and wondering if other states handle it differently.

Yes, it definitely varies by state. In Minnesota, you're required to complete Form M-24R specifically for real estate and M-24B for bulk sales of business assets, which is why your accountant needed to separate them. Some states like California and New York treat real estate and personal property completely differently for withholding purposes, while others like Florida and Texas don't have state income taxes so they don't impose this withholding at all. Illinois and New Jersey treat them similarly but require different reporting forms. The key is having the purchase agreement clearly itemize what portion of the sale price applies to personal property versus real estate.

For installment sales, most states apply the withholding requirement only to the payments you receive in the current tax year. So they would withhold from your down payment and any principal payments received before December 31st. The tricky part is that you'll need to continue dealing with withholding in future years as you receive additional payments. Some states have special installment sale forms that you file annually. Others require the buyer to withhold from each payment unless you get an exemption certificate. It's definitely more complicated than a standard sale, and you might want to consult with a tax professional who specializes in installment sales.