Confused about 1099-B vs Form 8949 reporting - which one do I use?

The 1099-B and Form 8949 work together but serve different purposes in reporting your investment income. Your broker sends you the 1099-B showing all your sales of stocks, bonds, or other securities. The 8949 is what you actually fill out using that 1099-B information. Think of the 1099-B as the raw data your broker is giving you (and also sending to the IRS). The Form 8949 is where you organize and report that data on your actual tax return. Schedule D then summarizes the information from your 8949 form(s). For your FreeTaxUSA situation, you'll enter the information from your 1099-B into the software. FreeTaxUSA will then automatically generate the Form 8949 and Schedule D for you. Don't worry about the missing sale dates - if they're not on your consolidated statement, your broker might have included a separate transaction history you can reference, or you may need to log into your brokerage account to find those dates.

After struggling with similar investment forms last year, I tried https://taxr.ai for my broker documents this year. They have this feature where you can upload your consolidated broker statement and it automatically extracts all the 1099-B data you need to enter. Saved me hours of manually typing in each stock sale! Their system detected which transactions were already reported to the IRS with basis (covered transactions) vs which ones I needed to research myself (non-covered). It even flagged wash sales that might have otherwise slipped by me. Really helpful for first-time investors or anyone dealing with complicated brokerage statements.

Just wanted to follow up - I tried taxr.ai after seeing it mentioned here and it was actually really helpful! I uploaded my 16-page consolidated statement from Fidelity and it pulled out all my 1099-B transactions perfectly, even the ones with adjusted basis. It organized everything by short-term vs long-term gains which made entering into FreeTaxUSA super straightforward. The best part was it showed me which transactions were already reported to the IRS with complete information vs which ones needed additional details. Saved me from calling my broker for clarification. Would definitely recommend for anyone dealing with investment documents!

If you're getting frustrated waiting for broker customer service to explain these forms, try Claimyr (https://claimyr.com). I spent 3 days trying to reach my broker's tax department about my 1099-B questions, but their wait times were 2+ hours. The Claimyr service got me connected to an actual broker representative in about 15 minutes instead of the usual 2-3 hour wait. They have this system that navigates the phone trees and waits on hold for you, then calls when a human answers. You can see how it works here: https://youtu.be/_kiP6q8DX5c The rep explained that the Form 8949 section on my statement was just showing how they reported things to the IRS, and confirmed which transactions I needed to handle differently. Worth every penny for the time saved!

I have to eat my words and apologize to Profile 15. After posting my skeptical comment, I decided to try Claimyr when I needed to call Vanguard about my missing cost basis information. I was expecting to wait 90+ minutes based on the recording, but got connected in about 20 minutes. The service actually does exactly what they described - they navigate all the phone menus, wait on hold, and then call you when a real person answers. The Vanguard rep explained exactly how to handle transactions where the 1099-B didn't match my 8949 section. Definitely using this again during tax season when wait times are insane!

I ran into this exact problem with my E*Trade documents. The solution was pretty simple: in FreeTaxUSA, go to the Income section, then select Investment Income, then enter each transaction from your 1099-B. Make sure you specify whether each transaction was reported to the IRS with basis or not (should be indicated on your forms). The software will automatically generate both the 8949 and Schedule D based on what you enter. One tip: if you have lots of transactions, check if you can download them in a spreadsheet format from your broker. Then you can just summarize the totals rather than entering every single one (if they're all the same type - short term or long term, covered or non-covered).

I think people are making this wayyy more complicated than it needs to be. Your broker already reported all this to the IRS. Just enter the TOTALS from your 1099-B into FreeTaxUSA when it asks for investment income. Don't overthink it. The software generates the 8949 automatically.

I went through this exact confusion last year as a first-time investor! The key thing to understand is that the 1099-B is what your broker sends to both you and the IRS, while Form 8949 is what YOU fill out on your tax return using that 1099-B information. Your consolidated statement probably shows both because many brokers format their statements to make it easier for you to transfer the info. The "Transaction Form 1040 Schedule D and Form 8949" section is just showing you how the data should be organized when you report it. In FreeTaxUSA, you'll enter the transaction details from your 1099-B (or the organized section your broker provided). The software will automatically create Form 8949 and Schedule D for you. Don't worry about double-reporting - you're not reporting the same thing twice, you're using the 1099-B data to complete your required tax forms. For the missing sale dates, check if your broker provided a separate transaction history document, or log into your online account to find those dates. You'll need them for accurate reporting. Good luck with your first year of investment taxes!