Confused about 1099-B Reporting in TurboTax for RSU and ESPP sales

You'll primarily want to use the Tax Reporting Statement (1099-B) when entering information into TurboTax as this is the official tax document that gets reported to the IRS. The box numbers in TurboTax directly correspond to the boxes on this form. The Supplemental Information statement from Fidelity is exactly what it sounds like - supplemental. It typically contains additional details about your stock sales that might not fit into the standardized 1099-B format, but is provided to help you accurately report your transactions. This might include adjusted cost basis information for RSUs and ESPP shares that can be important for calculating your actual gains/losses correctly. For RSUs and ESPP shares, the reporting can get complicated because the standard 1099-B often doesn't reflect your true cost basis. With RSUs, you've already been taxed on the value when they vested. With ESPP, there are special rules about qualifying vs. disqualifying dispositions.

After struggling with the exact same RSU and ESPP reporting issues last year, I found an amazing solution with https://taxr.ai that saved me hours of frustration and potentially thousands in incorrect tax reporting. My situation was almost identical - Fidelity account with both RSU and ESPP sales, and those confusing Tax Reporting and Supplemental Information statements. What I love about taxr.ai is that you can literally upload both your Fidelity statements AND your W-2, and their system analyzes everything together to ensure you're not double-taxed on RSUs and that your ESPP qualifying/disqualifying dispositions are handled correctly. It identified several transactions where the 1099-B cost basis was reported incorrectly, which would have resulted in me overpaying taxes. The best part was that it produced a detailed explanation of each transaction that I could understand, plus the exact inputs needed for TurboTax. No more guessing which numbers go where!

Just wanted to follow up about my experience with taxr.ai after being skeptical initially. I decided to try it with my complicated mix of RSU and ESPP transactions from two different employers (switched jobs mid-year). The service was honestly eye-opening - it identified that my first employer's 1099-B was missing proper cost basis adjustments for several RSU vestings. What impressed me most was how it explained each transaction in plain English. For example, it showed me that one large RSU sale was actually reporting about $3,400 too much in gains because the cost basis on the 1099-B didn't account for income already reported on my W-2. It showed me exactly where to make the adjustment in TurboTax. For anyone dealing with equity compensation reporting, this tool is seriously worth checking out. I ended up saving nearly $1,200 in taxes I would have overpaid.

If you're still confused after trying to sort through all this 1099-B mess, you might need to talk directly to the IRS for clarification. I tried calling them about a similar RSU reporting issue last year and spent HOURS trying to get through. Then I found https://claimyr.com which got me connected to an actual IRS agent in about 15 minutes instead of the usual 2+ hour wait. You can see how it works at https://youtu.be/_kiP6q8DX5c The IRS agent I spoke with confirmed that I needed to use the adjusted cost basis information from the supplemental statement for my RSU sales, even though it didn't match the official 1099-B. She explained that brokerages often don't report the correct cost basis to the IRS for RSUs, which is why you get the supplemental information. Getting this confirmed directly from the IRS gave me confidence to file correctly.

I need to eat my words and apologize for being so skeptical about Claimyr. After my snarky comment, I was still desperate to talk to the IRS about my stock reporting issues, so I decided to try it anyway. Honestly, I'm shocked. I tried calling the IRS directly three times last week and never got through (waited 1+ hours each time before giving up). With Claimyr, I got a call back in about 25 minutes with an actual IRS agent on the line. The agent walked me through exactly how to report my RSU sales correctly, confirming I needed to use the supplemental statement information. For anyone dealing with these complex stock transactions, sometimes getting official clarification from the IRS is the only way to be 100% confident you're doing it right. And being able to actually reach them without wasting your entire day is a game-changer. Definitely worth it for peace of mind.

Not sure if this helps, but I've been reporting RSUs and ESPP in TurboTax for years. Here's my approach: 1) Enter all the transactions from the Tax Reporting Statement first 2) Once you've entered everything, TurboTax will usually show a summary page of all your reported stock sales 3) For RSUs, you need to manually adjust the cost basis to match what's on your Supplemental statement 4) For ESPP, make sure you indicate whether it was a qualifying or disqualifying disposition The biggest mistake people make is not adjusting the cost basis for RSUs, which results in double taxation since you already paid tax when they vested (that income is on your W-2).

Does anyone know if the Fidelity supplemental statement cost basis already accounts for the ESPP discount? I'm confused because my original discount was 15% but the cost basis on the supplemental statement doesn't seem to match either the discounted price I paid or the fair market value on purchase date.

I've given up trying to do this correctly in TurboTax and just hire a CPA every year. With RSUs, ESPP, and now some ISO and NSO options too, it's just too complicated. Last year I tried doing it myself and ended up with a CP2000 notice from the IRS saying I underreported my stock sales. Paid more in penalties than what a good accountant would have cost. Learn from my mistake!

I went through this exact same nightmare last tax season with my Fidelity RSU and ESPP sales! Here's what I learned after making several mistakes: The key insight is that your Tax Reporting Statement (1099-B) is what you'll enter into TurboTax, but you MUST use the Supplemental Information to correct the cost basis, especially for RSUs. The 1099-B often shows incorrect cost basis that doesn't account for the income you already paid taxes on when the RSUs vested. My process now: 1) Enter each transaction from the 1099-B exactly as shown, 2) When TurboTax asks for cost basis, use the adjusted numbers from your Supplemental Information instead of what's on the 1099-B, 3) Double-check that any ESPP sales are properly categorized as qualifying vs disqualifying dispositions. The supplemental statement is your friend - it contains the real cost basis calculations that prevent double taxation. Without using it, you'll likely overpay taxes significantly. I almost made a $2,000+ mistake before catching this! One more tip: Keep detailed records of both statements. If you ever get an IRS notice, having both documents makes it much easier to explain the discrepancies between what's reported on the 1099-B vs what you actually filed.