I used H&R Block last year with about $200k in RSUs and they completely missed some important details. The preparer didn't understand that I needed to report the sales of vested RSUs as capital gains transactions with the correct cost basis. Ended up filing an amended return later with a different tax service. Would not recommend for anything beyond basic RSU situations.

That's not correct for RSUs. The 83(b) election applies to restricted stock awards (RSAs), not restricted stock units (RSUs). With standard RSUs, you can't make an 83(b) election because there's nothing to elect - you don't actually receive the shares until they vest, so there's no ownership to claim early. Some companies offer early-exercisable options or RSAs where an 83(b) makes sense, but for standard RSUs, this isn't applicable. Important distinction that could cause tax issues if misunderstood.

Thanks for mentioning this! I didn't even think about the asset list. Do you know if there's a standard format for this? And for the customer concentration report, did you just create a spreadsheet or is there a more official way to present that information?

For the asset list, I just created a simple spreadsheet with columns for: description, date acquired, original purchase price, current estimated value, and condition (excellent, good, fair, etc.). Nothing fancy, but buyers appreciated the organization. The customer concentration report was also just a spreadsheet showing my top 10 customers, what percentage of revenue each represented, how long they'd been customers, and brief notes about the relationship. My broker actually said these simple documents made a huge difference in buyer confidence because they showed I was organized and transparent.

Is there an easy way to calculate this? I've owned my S-corp for 12 years and honestly have no idea what my current basis is.

I haven't considered electing to be treated as a corporation - could you explain a bit more about when that might be advantageous for investment activities? Would the corporate tax rates be better than the withholding rates in some cases? And would I still need to file Form 5472 if I made that election?

Making an election to be treated as a corporation (Form 8832) can sometimes be advantageous because U.S. corporate tax rates might be lower than the withholding rates applied to foreign persons, especially for certain investment types. For example, while dividends are typically subject to 30% withholding (or lower with tax treaties), the corporate income tax rate is 21%. Yes, you would still need to file Form 5472 if you made the election, as it applies to 25% foreign-owned U.S. corporations. However, instead of filing a pro-forma 1120, you'd file a regular Form 1120 as an actual tax return. Another benefit is that a corporation can potentially claim deductions against income that might not be available to a foreign person receiving passive income. The downside is increased compliance requirements and potential for double taxation if you eventually distribute earnings to yourself. The optimal structure really depends on your specific situation, investment amounts, and how your country's tax treaty interacts with U.S. tax law.

I've had an account with Interactive Brokers for my foreign-owned Delaware LLC for about 3 years now. They're definitely more accommodating to international structures than many other brokerages. The documentation requirements were still extensive, but their system is set up to handle foreign ownership situations. They also have good systems for handling tax withholding based on tax treaty status.

Yeah I did get a confirmation email from TurboTax when I made the payment, but it was just saying they submitted it - not that the IRS actually received it. Should I be getting something directly from the IRS too?

Yes, you should have received a confirmation directly from the payment processor the IRS uses, not just from TurboTax. When you pay through TurboTax, they typically redirect you to an IRS-authorized payment processor, which should provide its own confirmation number. I'd recommend logging into your TurboTax account and checking the payment details section. There should be information about how your payment was processed and possibly a second confirmation number from the actual payment processor. If you can't find this, you might want to contact TurboTax support to get the payment confirmation details.

This is the right answer. I check my transcript every year. The transaction codes tell you everything - way more reliable than calling or using Where's My Refund.

Thanks! Yeah I've found the transcript to be the most reliable source of information. The IRS website isn't the most user-friendly, but once you learn how to read the transaction codes, it's actually pretty straightforward. For anyone looking for this information, you want the "Account Transcript" specifically, not the "Return Transcript" - they're different documents in the IRS system.

Oh no, I might have missed the deadline for 2020 then! Does the IRS ever make exceptions for people who didn't know about the 3-year rule? And just to clarify, even if I can't get a refund for the older years, I should still file those returns anyway, right?

Unfortunately, the IRS is very strict about the 3-year refund statute and doesn't make exceptions even if you didn't know about the rule. It's set by law, not IRS policy, so they can't bend it. Yes, you should still file all unfiled returns even if you can't get the refund anymore. This closes your file with the IRS and prevents future issues. While you won't get money back for those older years, filing completes your tax record and can help with things like loan applications, government benefits, or any situation where tax return information is needed. Better to have everything clean and complete than leave those old years hanging.

Free File Fillable Forms only work for the current tax year (so right now, only 2024). For prior years, you need to download the specific forms for those tax years from the IRS website and mail them in. I did this last year for my 2021 and 2022 returns. You can still use free tax software though! Most of the major companies (TurboTax, H&R Block, TaxSlayer) offer access to prior year returns on their websites. The catch is that you can prepare them for free, but they usually charge to file them. Since you have to mail prior year returns anyway, you can just print them out and mail them yourself without paying.