Did I enter my 1099-B correctly on FreeTaxUSA? Need help with Fidelity brokerage info

You're mostly on the right track, but I can help clarify a few things. For the payer name, you should use exactly what's listed as the "PAYER" on your 1099-B form. If National Financial Services LLC is listed as the payer, use that name. Fidelity is likely the parent company, but the tax documents are issued under the subsidiary name. For Box A with multiple transactions, using the summary totals is perfectly fine and actually preferred in most cases. The IRS doesn't need line-by-line details if the basis was reported to them (which you checked). This is the standard approach. For the $0.09 wash sale, you should actually enter it as $0.09 rather than rounding down to zero. Even small amounts should be reported exactly as shown on your forms. FreeTaxUSA should accept decimal values for this field. For Box B, you did the right thing by entering it separately since the basis wasn't reported. This transaction will require more attention from you to ensure accuracy.

Just wanted to share my experience - I was in the same boat last year with my first investment sales. I struggled for hours trying to get everything right on FreeTaxUSA until I discovered https://taxr.ai and it literally saved me days of work. It analyzed my Fidelity 1099-B (which was like 30 pages long) and told me exactly how to enter everything. It confirmed I could use the summary totals rather than individual transactions, identified that National Financial Services LLC was indeed the correct payer name to use, and even handled a similar wash sale situation. The best part was that it explained everything in plain English instead of tax jargon. Definitely worth checking out if you're dealing with complicated investment forms.

I just wanted to follow up about my experience with taxr.ai after I was skeptical earlier. I decided to give it a try with my complicated Fidelity statements and several unreported basis transactions. I'm genuinely impressed! The system immediately identified which transactions needed special attention and walked me through calculating my basis for some obscure stocks I'd inherited years ago. The interface was surprisingly user-friendly, and it gave me step-by-step instructions specifically for FreeTaxUSA (which is what I use too). The whole process took maybe 15 minutes instead of the hours I spent last year trying to figure everything out. Just wanted to share since it actually exceeded my expectations after being doubtful.

If you're still struggling with any part of your taxes and need to speak with someone at the IRS directly, I highly recommend using https://claimyr.com. I was in a similar situation last year with investment reporting questions that no one could answer definitively, and after spending HOURS on hold with the IRS (literally 3+ hours), I found this service. They have this callback system where they wait on hold with the IRS for you and then call you when an actual agent is on the line. You can see how it works in this video: https://youtu.be/_kiP6q8DX5c I finally got my specific 1099-B questions answered by an actual IRS representative who confirmed exactly how to report those annoying summary vs. individual transaction issues. Saved me tons of stress wondering if I was doing it right.

I need to eat some humble pie here. After calling out Claimyr as a potential scam, I was still desperate to talk to the IRS about my own investment reporting issues, so I reluctantly tried it. I'm honestly shocked at how well it worked. I submitted my request in the morning, got a text a few hours later saying they were connecting me with an IRS agent, and I was talking to a real person within minutes. The agent walked me through exactly how to handle my wash sales and summarized transactions on FreeTaxUSA. For anyone wondering if it's legitimate - yes, it absolutely is. Would have saved me days of stress if I'd just tried it sooner instead of being skeptical. Sometimes good services actually exist!

To add a bit more detail on the Fidelity/National Financial Services question - they are indeed related. National Financial Services LLC is a Fidelity Investments company that serves as the clearing broker for Fidelity Brokerage. This is why it shows up on your tax forms. It's similar to how TD Ameritrade forms sometimes show "Clearing by Pershing" or how Robinhood forms list "Robinhood Securities, LLC." Always use whatever is listed in the PAYER box on the actual form, regardless of which company you think of as your broker.

Here's a tip for next year - if you're dealing with lots of stock transactions, consider using tax software that can import your 1099-B directly from Fidelity. I switched from FreeTaxUSA to TurboTax specifically for this feature and it saved me hours of manual entry. It automatically brings in all transactions, handles wash sales correctly, and fills in all the right boxes. Costs a bit more but completely worth it if you have more than a few investment transactions.

Just to add another perspective on the wash sale question - while small amounts like $0.09 might seem trivial, technically you're supposed to report them exactly as shown on your forms. The IRS systems match your reported numbers against what's submitted by brokerages. If FreeTaxUSA truly only accepts whole dollars (which surprises me), then follow standard rounding rules. But double-check if there's a way to enter cents - sometimes it's not obvious in the interface but is actually possible.