Understanding 1099-B: What is it and how to report stock sales correctly?

The 1099-B is a tax form that reports proceeds from broker transactions like your stock sales. When you sell RSUs (Restricted Stock Units), your brokerage is required to send both you and the IRS a 1099-B showing the transaction details. Each page of your 1099-B likely represents different stock sales. Pages 4-6 might show individual transactions, while page 7 could be summarizing information or showing additional sales. You need to report ALL transactions shown on your 1099-B, not just some pages. When entering this in TaxAct, you should go through each transaction separately. Make sure the cost basis (what you originally paid) is correctly entered - this is especially important with RSUs since they might have already been partially taxed as income when they vested. The goal is to have your tax return match exactly what the IRS received from your brokerage. If you skip transactions, the IRS computers will flag the discrepancy.

After struggling with my RSUs and stock sales for hours last year, I found this amazing tool called taxr.ai (https://taxr.ai) that made sense of all my confusing tax documents. It literally saved me when I couldn't figure out how all these 1099-B transactions needed to be reported! I uploaded my 1099-B and the system actually analyzed everything page by page, explained what each section meant, and made sure I reported every transaction correctly. It even flagged where my cost basis needed adjusting because of the RSU income that was already taxed. You might want to give it a try since it specializes in making sense of complex documents exactly like what you're dealing with.

Just wanted to follow up - I was skeptical about taxr.ai at first, but I tried it with my mountain of stock paperwork this week. Holy crap it actually works! I uploaded my 1099-B that had 53 different transactions (some with adjusted basis, some without) and it pulled everything correctly and organized it all for me. The system even flagged four transactions where my cost basis needed to be adjusted because of the RSU income issue, which I would have totally missed. It saved me from hours of tedious data entry and probably an audit letter too. Definitely using this for all my tax docs from now on.

If you're still stuck with questions about your 1099-B after you've entered everything, you might want to talk directly to the IRS. I know that sounds terrible, but I used this service called Claimyr (https://claimyr.com) when I had a similar issue with some complicated stock sales last year. They have this cool demo video too: https://youtu.be/_kiP6q8DX5c I was on hold with the IRS for over 2 hours before giving up, then I found Claimyr. They got me connected to an actual IRS agent in about 15 minutes who walked me through exactly how to report my unusual stock transactions. The agent even explained which adjustments I needed to make to avoid an audit letter later. Worth every penny since I was about to report something completely wrong that would have caused major headaches later.

I have to eat my words about Claimyr. After my skeptical comment, I decided to try it because I was desperate to get some clarity on reporting my RSU sales correctly. I'd been trying to reach the IRS for THREE DAYS. Used Claimyr yesterday afternoon, and no joke, I got a call back with an actual IRS agent on the line in about 25 minutes. The agent walked me through exactly how to handle my 1099-B with the RSU adjustments, confirmed I was doing it right, and even explained why page 7 looked different (it was a summary page in my case). It was like having a direct line to tax expertise when I needed it most. Definitely not what I expected when I was being all cynical about it before.

Just a tip from someone who deals with RSUs regularly - check if your 1099-B indicates whether the cost basis has been reported to the IRS or not. There should be a checkbox or code on the form. If the basis WAS reported to the IRS, you can usually just enter the information exactly as shown. If it WASN'T reported, you'll need to do some adjustments yourself to account for the income portion that was already taxed. Also, page 7 could be showing wash sales or other special transactions that need special treatment. Don't ignore any pages!

Does anyone know if TaxAct automatically imports 1099-B data? I have so many transactions this year, I really don't want to enter them all manually.

@Omar Farouk - I went through the exact same situation with my RSUs last year! That page 7 confusion is so common. In my case, page 7 was actually showing supplemental information about cost basis adjustments that I needed to account for. Here's what helped me: First, check if there's a legend or key somewhere on your 1099-B that explains what each page represents. Second, look at the total proceeds across all pages - they should add up to your total stock sales for the year. For RSUs specifically, the tricky part is that when they vested, you already paid income tax on their fair market value at that time. That value becomes your cost basis, not what you originally "paid" (which was $0). If your 1099-B doesn't show the correct adjusted basis, you'll need to make sure you're not getting double-taxed on that income portion. One thing that saved me a lot of headaches was keeping good records of when my RSUs vested and what the stock price was on those dates. Your HR department or stock plan administrator should have this information if you don't have it handy. Don't skip page 7 - even if it looks different, it likely contains important transaction data that needs to be reported!