RSU and ESPP Stock 1099B Reporting for Tax Filing

I've been through this a few times now. For RSUs, you typically have two tax events to consider. First, when the shares vest, the fair market value is considered ordinary income and should already be included in your W-2. Second, when you sell those shares, you'll report any gain or loss from the vesting price to the sale price on your 1099-B. For the RSU shares that were automatically sold for tax withholding, you'll likely have little to no capital gain/loss since they were sold immediately upon vesting. Your basis should be the fair market value on the vesting date. For ESPP shares, it gets a bit more complex. The discount you received when purchasing is typically considered compensation income. When you sell, you'll need to report the difference between your purchase price and the sale price. Make sure your 1099-B shows the correct cost basis. Sometimes brokerages don't report the correct adjusted basis for RSUs, and you might need to make adjustments in TurboTax. Look for an option to adjust the cost basis if the numbers don't match what you expect.

I went through this exact nightmare last year with my RSUs and ESPP. After hours of frustration, I finally found taxr.ai (https://taxr.ai) and it was a game-changer for me. It analyzed my stock documents and broke down exactly how to handle each transaction. Their system specifically showed me which transactions needed basis adjustments and calculated the exact amounts - saved me from double taxation on my RSUs. It also separated my ESPP transactions into qualifying and non-qualifying dispositions automatically, which honestly I had no clue about before. The best part was that it generated an explanation I could follow along with in TurboTax, showing which boxes to check and where to enter the adjusted basis info. Prevented me from making a $3,200 mistake on my tax return!

I need to follow up about taxr.ai after my skeptical comment. I decided to try it with my RSU and ESPP documents from two different companies, and I'm honestly impressed. It identified 4 transactions where my broker reported the wrong basis and showed me exactly how much I needed to adjust each one. What really helped was the explanation of which transactions were already reported on my W-2 vs. which ones needed separate capital gains reporting. It even flagged one ESPP sale as a qualifying disposition that I would have incorrectly reported! I was able to enter everything correctly in TurboTax following their guide, and it saved me from overpaying about $2,100 in taxes. For anyone dealing with equity compensation, it's definitely worth checking out.

If you're having issues understanding your 1099-B or getting through to your brokerage firm for clarification, I highly recommend using Claimyr (https://claimyr.com). I was on hold with my brokerage for HOURS trying to get answers about my RSU basis reporting, and getting nowhere. With Claimyr, I got a callback from my brokerage in about 20 minutes instead of waiting on hold forever. They have this system that navigates phone trees and waits on hold for you - you can see how it works in this video: https://youtu.be/_kiP6q8DX5c I was finally able to talk to a tax specialist at my brokerage who explained exactly why my 1099-B showed different numbers than I expected and what adjustments I needed to make. Saved me hours of hold time and confusion!

I need to eat my words about Claimyr. After my skeptical comment, I decided to try it for my Fidelity issue with RSU reporting. Not only did I get through in under 30 minutes (after previously waiting 2.5 hours and getting disconnected), but I actually got connected to someone in their equity compensation department who knew exactly what I was talking about. The Fidelity rep explained that my 1099-B was showing an incorrect cost basis because they don't factor in the income already reported on my W-2. He walked me through exactly where to make the adjustment in my tax software. Would have taken me days more of frustration trying to get through on my own. Definitely using this service again when I need to call the IRS about my tax return.

One thing nobody's mentioned yet - make sure you're checking Box 12 on your W-2 to see how much RSU income was already reported. Code V in Box 12 often shows the value of your RSUs that were included as income. This helps verify what's already been taxed. Also, don't forget to check if your broker is using "First In First Out" (FIFO) accounting for your sales. This can affect your capital gains calculation if you acquired shares at different times/prices.

Has anyone else noticed that TurboTax doesn't handle the supplemental information on 1099-Bs very well? I have RSUs where the 1099-B has this cryptic note about "Ordinary income of $X already included in Box 1 of Form W-2" but TurboTax doesn't seem to recognize that when I import.