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.

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.

Thanks for this suggestion! I didn't even know I could request a transcript. Will this show pending actions on my account too, like if they're actually processing a lien? And how far back does it go - will it show the original CP2000 issue from 2017?

Yes, the account transcript will show pretty much everything related to that tax year, including the CP2000 adjustment, any penalties or interest assessed, and your payment. It should also show any collection actions being considered or initiated. The transcript goes back the full timeline for that specific tax year, so your 2017 transcript will show everything from when you first filed that return up through current actions. When you request it, make sure you're getting the "account transcript" specifically (not just the "tax return transcript") and for tax year 2017. This is the most comprehensive record of all transactions and will be your best evidence if you need to dispute anything.

I did this last year for a payment issue. You need to schedule an appointment first (can't just walk in) by calling 844-545-5640. They were able to pull up my account and confirm my payment had been received. Took about 2 weeks to get an appointment but the actual visit was only about 30 minutes.

Thanks for the tip about needing an appointment. Did they actually resolve your issue during the visit or did you still have to wait for processing? I'll try calling that number tomorrow to schedule something.

That's a great point I hadn't considered. I acquired the shares in three different grants over about 2 years, with different purchase prices. Would I need to specifically tell my broker which lots to sell, or is that something I can handle when I file my taxes?

You need to specify which lots you want to sell at the time of the sale - you can't decide later when filing taxes. Most online brokerages have this option during the trade execution process, usually called "tax lot selection" or something similar. If your broker's online platform doesn't make this obvious, call their customer service before placing the trade. Once the trade settles, you typically can't change which lots were sold, so it's important to get this right the first time. This kind of specific lot identification can make a substantial difference in your tax situation.

This is good advice. You can offset up to $3k of ordinary income per year with capital losses beyond what you use to offset gains. So if OP doesn't need to offset all $87k in gains this year, they could realize some losses now and carry the rest forward.