One thing nobody has mentioned yet - the company might have had a reason for issuing a 1099-NEC. Was there any chance this was structured as a buyback with an additional premium? Sometimes companies will pay more than fair market value for shares as a form of severance or additional compensation, especially with early employees. If that's the case, you might need to split the reporting - part as capital gains (the actual FMV of the stock) and part as compensation (any premium above FMV). Worth double-checking your sale documents to confirm the valuation matched pure FMV.

Just a heads up - I dealt with this exact issue last year with QSBS stock. Make absolutely sure you have documentation proving it qualifies as QSBS! The requirements are strict: - Company must be a qualified small business when you acquired the stock - Must have held the stock for at least 5 years - Company assets must have been under $50 million when stock was issued - Must be original issue stock (bought from company, not secondary) The IRS scrutinizes QSBS claims carefully because of the huge tax advantage. If you're claiming the 50% exclusion, make sure you have rock-solid proof for every QSBS requirement.

11 Does anyone know if there's a time limit for using these carried-over investment interest expenses? I have some from like 5 years ago that I haven't been able to use yet.

This thread has been incredibly helpful! I'm in a similar situation with investment interest carryovers and want to add a few practical tips for anyone else dealing with this: 1. **Keep meticulous records** - The IRS doesn't track your carryovers for you, so maintain copies of all Form 4952s that show disallowed amounts. I create a simple spreadsheet tracking carryover amounts by year. 2. **Review your investment strategy** - If you consistently have more investment interest expense than investment income, consider whether the debt is truly worth it from a tax perspective. 3. **Consider timing** - If you're close to the standard vs. itemized deduction threshold, sometimes it makes sense to bunch investment expenses (and other itemizable deductions) into alternating years to maximize the benefit. The indefinite carryforward rule is really generous compared to other tax provisions, so don't let these deductions go to waste! Just make sure you have the documentation to back them up.

Another approach I used last year was attaching my § 1.351-3 statement as a PDF within the "Miscellaneous Statements" or "Additional Information" section in TurboTax. I labeled it clearly and made sure to reference it in the main form where relevant. My return was accepted without issues. I also kept a paper copy of everything, including the statement, just in case the IRS requested additional information. They never did, which suggests the e-filed statement was sufficient.

Does anybody know if there are specific penalties for not including this statement? I realized I needed to file one for a transaction I did in 2022, but I've already filed my taxes for that year and don't want to deal with an amended return if the penalties are minimal.

One thing I learned the hard way - make multiple copies of everything before sending! I sent my 83(b) election last year from Japan, and the IRS claimed they never received it despite tracking showing it was delivered. Send it with tracking for sure, but also keep digital scans of everything you submit, including proof of mailing and delivery confirmation. This documentation saved me during an audit when the IRS couldn't locate my original 83(b) election in their records.

As someone who's been through this exact scenario (non-resident working for US company with stock options), I can confirm that yes, you absolutely need to file the 83(b) election even as a Brazilian non-resident. The US will still consider this US-source income when you eventually exercise or sell. A few practical tips from my experience: 1. You can file the 83(b) election before getting your ITIN - just include a note that your ITIN application is in process. The IRS accepts this. 2. For mailing from Brazil, use a reliable courier service like DHL or FedEx with tracking. Regular mail is too risky for something this important. 3. The correct address for international filers is: Internal Revenue Service, Austin Service Center, ITIN Operation, P.O. Box 149342, Austin, TX 78714-9342 4. Include a cover letter explaining you're a non-resident filing an 83(b) election, and request written confirmation of receipt. The 30-day deadline is absolute, so don't delay! Also consider consulting with a tax professional who understands both US and Brazilian tax law, especially since Brazil doesn't have a comprehensive tax treaty with the US - you'll want to plan for potential double taxation issues down the road. Good luck!

Is anyone using TurboTax or other tax software that helps with penalty abatement requests? I'm wondering if I need to hire a professional or if I can handle this myself.

This is incredibly useful information! I wish I had known about penalty abatement options earlier. I've been dealing with a failure-to-pay penalty from 2022 when I had to choose between paying my mortgage and paying my quarterly taxes after losing my job unexpectedly. I ended up paying the taxes late once I found new employment, but the penalties have been accumulating with interest. Based on what's been shared here, it sounds like I might qualify for reasonable cause abatement since job loss is typically considered a circumstance beyond my control. Quick question for the tax professionals here - when documenting job loss for reasonable cause, what kind of supporting documentation works best? I have my termination letter and unemployment benefit records. Would those be sufficient, or do I need additional proof that the job loss directly impacted my ability to pay on time? Also, does anyone know if there's a statute of limitations on requesting penalty abatement? It's been about 2 years since the penalties were assessed.