Is this different from the normal process of just filing back taxes? Like do you have to specifically enroll in a program or something?

The Voluntary Disclosure Practice is different from simply filing past due returns. It's a more formal process where you're specifically disclosing potential tax violations before the IRS discovers them. For most people who have simply failed to file but don't have complex tax situations or intentional fraud, just filing the past due returns is usually sufficient. The IRS generally looks favorably on taxpayers who file missing returns without being prompted. The formal Voluntary Disclosure Program is typically more relevant for situations involving offshore accounts, intentional evasion, or potential criminal exposure.

Omg that's terrifying. Did they have to pay it all at once or could they set up some kind of payment plan?

Their regular support is useless for this, but I paid extra for TurboTax Live last year and got connected with a CPA who actually knew about RSUs. She walked me through exactly where to make the adjustments in the software. Worth the upgrade if you're dealing with this regularly. She also helped me create a spreadsheet to track my RSU basis for future years, which has saved me tons of time.

Thanks for the tip about TurboTax Live! I'll give that a try. I've been thinking about switching to a CPA but they're so expensive in my area. A middle ground like this might be perfect.

This is super helpful - thank you! I just checked and my 1099-B does have that box checked. I'll make sure to use the adjustment code when I'm fixing this in TurboTax. Is this something that the IRS commonly flags? I'm worried about getting some kind of automated notice even if I do everything correctly.

It is something the IRS automated system flags if you don't handle it correctly, which is why using the proper adjustment code is important. Their matching system will compare your 1099-B to what you report, and if you don't explain the discrepancy properly, it can trigger a notice. But if you use code B on Form 8949 and include the explanation statement that TurboTax generates, you should be fine. I've been reporting RSUs this way for 5 years and never had an issue. The key is making sure you have documentation of your cost basis (like that supplemental tax form from your brokerage) in case you ever need to prove it.

Did you find any deductions or credits you were missing when you switched? My biggest fear is leaving money on the table by doing it myself.

I actually discovered I qualified for the Saver's Credit that my tax preparer had missed the previous two years! It's for retirement contributions if you're under certain income limits. FreeTaxUSA has a good review system that checks for credits you might qualify for based on your inputs. It asks questions throughout that help identify potential deductions. In my experience, it was actually more thorough than my preparer who was rushing through multiple clients' returns during tax season.

I've used both. TurboTax has a slicker interface but FreeTaxUSA is MUCH cheaper and does everything you need. TurboTax charges extra for homeowner stuff and childcare credits (they put it in their "Deluxe" tier). With FreeTaxUSA all those forms are included in the free federal filing. For your situation, you'd probably end up paying $120+ with TurboTax vs. about $25 total with FreeTaxUSA (free federal + state fee). The questions and guidance are very similar between them.

Can you explain more about how to calculate which is better? I paid about $12,000 in tuition for my master's degree in 2019, and I'm trying to figure out if I should amend.

Sure! The calculation depends on your tax situation and what education expenses you had. For a master's degree, you wouldn't qualify for the American Opportunity Credit (it's only for undergrad), so you're choosing between the Lifetime Learning Credit and the tuition deduction. With $12,000 in qualified expenses, you could claim a Lifetime Learning Credit of 20% of that amount, up to the maximum of $2,000. So your LLC would likely be the full $2,000. For the tuition deduction, you could deduct up to $4,000, but the tax savings depend on your tax bracket. If you're in the 22% bracket, that's a savings of $880. In the 24% bracket, it's $960. So in your specific case with graduate school expenses, the Lifetime Learning Credit would likely be more beneficial than the tuition deduction.

You need to file separate 1040-X forms for each tax year. I did this last month for both 2018 and 2019. Make sure to mail them in separate envelopes too, as they go to different processing centers depending on the tax year.

Thanks, this is really interesting! I hadn't heard of the Series LLC before. Is this available in most states? And would each owner still get a K-1 showing their specific income after their individual expenses?

Series LLCs are currently available in about 20 states including Delaware, Texas, Illinois, and Nevada (among others), but the laws vary significantly by state. Even if your state doesn't allow them, you can form one in a state like Delaware and register it as a foreign entity in your home state, though this adds some complexity. Each owner would still receive a K-1 reflecting their share of income based on the operating agreement terms. The operating agreement would specify how individual expenses are accounted for before calculating each person's distributive share. This approach gives you the liability benefits of separate entities with the administrative simplicity of a single filing.

I wouldn't recommend a general partnership for this scenario. Without the LLC structure, all partners have unlimited personal liability for business debts and legal issues. That's a huge risk with 10 different people involved who all have separate business activities! An LLC provides crucial liability protection that a plain partnership doesn't.