Do I still need to file 1099-B if company stock was reported as income on my W2?

Thanks for the explanation, but I'm still confused. If I report both the W2 and 1099-B, isn't that reporting the same income twice? Also, how exactly do I fill out the basis section on Form 8949 since the stock was already taxed as income?

You're not reporting the same income twice when done correctly. Your basis (cost) for the stock is the amount already included as income on your W2. When you report the sale on Form 8949, you'll include that W2 amount as your basis, which means you're only taxed on any gain above what was already reported as income. For Form 8949, you'll need to check Box F for "Adjustments," and use code "R" to indicate the basis was reported to the IRS. Then list your proceeds from the 1099-B, your basis (the amount that was on your W2), and calculate the difference as your gain/loss. Most tax software walks you through this pretty well if you indicate you had RSUs.

Does taxr.ai work with all the major brokerages? My company RSUs are through Fidelity and their 1099-B reporting is kinda confusing with all the different lots and dates.

I've seen a lot of these document review services pop up lately. What makes this one different? I'm worried about sharing all my tax docs with some random website.

Yes, it works with all the major brokerages including Fidelity. It actually helped me identify which specific lots were my RSUs versus other stock purchases I had made, which made reporting much clearer. Regarding security concerns, I had the same worries initially. What set taxr.ai apart for me was that they use bank-level encryption and don't store your documents after analysis. Plus they specifically have expertise with equity compensation like RSUs, ISOs and ESPPs which is more specialized than general tax prep services.

How does this actually work? The IRS phone system is basically impossible to navigate. Does this really get you through faster?

Sounds like a scam to me. Nobody can magically get through the IRS phone system. They probably just connect you with some "tax expert" who isn't even with the IRS.

It works by essentially navigating the IRS phone system for you and holding your place in line. When they reach an actual IRS representative, they connect that person directly to your phone. It's not a separate service - you're actually talking to real IRS employees. The system uses automated technology to handle the waiting and navigation of the phone tree. Think of it like having someone else wait in line for you at the DMV and then texting you when it's your turn. It's completely legitimate - they just solved the waiting problem.

My broker (E*Trade) sometimes lists the basis and sometimes doesn't on RSU sales. Is there a way to know which reporting method they're using without calling them? My 1099-B is like 30 pages long with all my trades.

Look at Box 1e (Cost or other basis) on your 1099-B. If it shows $0 or a very low amount for your RSU sales, then your broker is using the non-adjusted basis method. If it shows an amount close to what you received when selling, they might be using the adjusted basis method. A quick way to check is to compare the amount in Box 1d (Proceeds) with the gain/loss reported - if the gain seems unusually large compared to your actual profit from the sale, they're probably reporting a non-adjusted basis. Most brokers include a supplemental statement explaining their reporting method somewhere in that 30-page document.

This is super important! My financial advisor told me this is one of the most common mistakes with RSUs. If the stock went up even a tiny bit between vesting and selling, that's a short-term capital gain. If it went down, that's a capital loss you can use to offset other gains.

That's exactly what happened with my RSUs! I vested 200 shares but only received about 130 after they sold some for tax withholding. So when I'm reporting the 1099-B, should I just focus on the shares I actually received and sold? Is there anything special I need to do about the ones that were sold for taxes?

You only need to report the shares you actually received and subsequently sold. The shares that were automatically sold for tax withholding were already properly accounted for by your employer - both the income and the withholding should appear on your W2. When you look at your 1099-B, it should only show transactions for the shares you controlled and decided to sell. Double-check the number of shares on your 1099-B matches what you expect (the vested amount minus what was withheld for taxes). This is another area where having all your documents in order helps tremendously.