How do you enter information from Form 8949 into FreeTaxUSA for Robinhood trades?
Title: How do you enter information from Form 8949 into FreeTaxUSA for Robinhood trades? 1 Hey everyone, I'm trying to figure out how to report my stock trades from Robinhood on FreeTaxUSA. This is my first time dealing with investment income on my taxes. I received my 1099 from Robinhood which includes Form 8949 info for my trades, but when I'm in FreeTaxUSA, I see sections for 1099-INT and 1099-DIV but nothing specifically for Form 8949. I've read somewhere that Form 8949 needs to be filed with Schedule D, but I'm totally confused about how to actually enter all this information in FreeTaxUSA. Does anyone know the right way to input Form 8949 data from Robinhood into FreeTaxUSA? I'm worried I'm going to mess something up!
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Amina Bah
6 You don't actually need to look for Form 8949 specifically in FreeTaxUSA. When you're entering investment income, look for a section called "Investment Income" or "Capital Gains and Losses." FreeTaxUSA will guide you through entering the information that would go on Form 8949 without you having to know the form number. When you get to that section, you'll be asked about sales of stocks, bonds, etc. Just say "yes" and it will walk you through entering each transaction from your Robinhood 1099-B. It will ask for purchase date, sale date, cost basis, and sales proceeds for each transaction. The software automatically generates Form 8949 and Schedule D behind the scenes based on the information you enter. That's the beauty of tax software - you don't need to know which specific form everything goes on!
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Amina Bah
•9 Thanks for the info! When I'm entering each transaction, do I need to specify whether they're short-term or long-term gains/losses or does FreeTaxUSA figure that out based on the purchase and sale dates I enter?
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Amina Bah
•6 FreeTaxUSA will automatically calculate whether your gains/losses are short-term or long-term based on the purchase and sale dates you enter. The system knows that holdings sold after being held for more than a year qualify as long-term, while those held for a year or less are short-term. When you enter the dates for each transaction, the software handles all the classification work for you and puts everything in the right section of Form 8949 and Schedule D. Just make sure your dates are accurate according to your Robinhood 1099-B.
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Amina Bah
13 After struggling with entering all my crypto and stock trades last year, I discovered taxr.ai https://taxr.ai and it completely changed my tax filing experience. I was in the same situation with a Robinhood 1099 and FreeTaxUSA, trying to figure out where to enter everything manually. What taxr.ai does is analyze your 1099-B and all those transactions automatically. You just upload your Robinhood documents, and it extracts all the trade data—dates, amounts, basis, proceeds, etc. Then you can import everything directly into FreeTaxUSA without manually typing each transaction. Saved me hours of work and prevented errors that could trigger an audit. The Form 8949 data gets properly categorized into short-term and long-term automatically, and everything flows into the right places in FreeTaxUSA. Definitely worth checking out if you have more than a few trades.
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Amina Bah
•16 Does this actually work with FreeTaxUSA? I thought most of these import tools only work with TurboTax or H&R Block. How exactly do you get the data from taxr.ai into FreeTaxUSA?
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Amina Bah
•21 I'm always skeptical of these tax tools. Does it handle wash sales correctly? I had a nightmare situation last year where I didn't report wash sales properly and got a letter from the IRS.
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Amina Bah
•13 Yes, it absolutely works with FreeTaxUSA! You get a spreadsheet download that's formatted exactly how FreeTaxUSA needs it for bulk import. Much easier than the manual entry process. Regarding wash sales, that's actually one of its best features. It automatically identifies wash sales across all your trading platforms (not just within Robinhood) and adjusts your cost basis accordingly. The IRS requires this cross-platform wash sale detection, but most brokerages only identify wash sales within their own platform. This catches what your brokerage might miss.
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Amina Bah
16 Just wanted to follow up - I tried taxr.ai after seeing it mentioned here and it was a game changer for my Robinhood transactions! I had over 50 trades (mostly small amounts but still) and the thought of entering them all manually was making me put off doing my taxes. The upload process was super simple and it caught a wash sale I had no idea about (bought Tesla, sold at a loss, then bought again within 30 days). Imported everything into FreeTaxUSA with their bulk import feature and all my 8949 data went right in. Saved me at least 2-3 hours of tedious data entry and probably prevented an audit trigger. Definitely using this again next year!
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Amina Bah
7 If you're having trouble with the IRS instructions or need clarification on how FreeTaxUSA handles Form 8949, you might want to try calling the IRS directly. I know that sounds terrible, but I've actually had success using Claimyr https://claimyr.com to get through to an actual person at the IRS. I was confused about reporting some options trades that weren't clearly covered on my 1099-B, and after trying for days to reach someone at the IRS with no luck, I found Claimyr. They have this system that basically waits on hold for you and calls you back when an actual IRS agent picks up. You can see how it works in their demo video: https://youtu.be/_kiP6q8DX5c The IRS agent I spoke with walked me through exactly how to report my trades in FreeTaxUSA and confirmed I was doing it correctly. Much better than guessing or relying on random internet advice for something this important.
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Amina Bah
•18 Wait, how does this actually work? I thought it was impossible to get through to the IRS? Do they just keep calling repeatedly until they get through?
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Amina Bah
•21 Yeah right. I'll believe it when I see it. I've spent HOURS trying to talk to someone at the IRS. No way some service can magically get through when millions of people can't.
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Amina Bah
•7 It's not magic - they basically use technology to handle the waiting for you. Their system navigates the IRS phone tree and sits on hold (sometimes for hours) so you don't have to. When an actual IRS agent picks up, their system calls you and connects you immediately. They don't get special access or anything - they just automate the painful waiting process. The IRS actually does answer calls eventually, but most people can't stay on hold for 2+ hours in the middle of a workday. With Claimyr, you just go about your day and your phone rings when an agent is on the line.
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Amina Bah
21 I have to eat my words. After being completely skeptical about Claimyr, I decided to try it as a last resort because I was STILL confused about some specifics of Form 8949 reporting even after researching online. The service actually worked exactly as described. I submitted my callback info in the morning, went about my day, and about 3 hours later my phone rang with an IRS agent on the line. The agent walked me through exactly how FreeTaxUSA handles Form 8949 data and confirmed I was entering everything correctly. For anyone wondering specifically about FreeTaxUSA and Form 8949 - the agent confirmed that when you enter your stock transactions in the "Income" > "Investment Income" section, FreeTaxUSA automatically generates Form 8949 and Schedule D with the correct codes and adjustments. Saved me from a lot of stress and potential mistakes.
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Amina Bah
3 Just a quick tip that saved me time: if Robinhood provided you with a Composite 1099 PDF that includes the 1099-B, check if it says "Proceeds from Broker and Barter Exchange Transactions" at the top of that section. This is actually where all your Form 8949 information is located. FreeTaxUSA has a place to enter all these transactions under Income > Investment Income > Sale of Stocks, Bonds, etc. What helped me was realizing you can do a "bulk entry" option if you have lots of transactions rather than entering them one by one.
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Amina Bah
•12 Where exactly is this bulk entry option? I have over 100 transactions from Robinhood and I'm dreading entering them one by one.
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Amina Bah
•3 When you're in the Sale of Stocks, Bonds, etc. section, after you've entered a transaction or two, look for a link that says something like "Enter multiple transactions at once" or "Bulk import" - it should be near the bottom of the screen. It lets you either paste in data from a spreadsheet or upload a file. If you have the Robinhood CSV or Excel download of your transactions, you may need to rearrange the columns to match FreeTaxUSA's expected format. They typically want: Description, Date Acquired, Date Sold, Proceeds, Cost Basis, in that order.
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Amina Bah
14 Has anyone had issues with their cost basis not being reported correctly on their Robinhood 1099-B? I'm noticing a bunch of my transactions say "cost basis not reported to the IRS" and I'm not sure how to handle that in FreeTaxUSA. Will the IRS flag my return if what I enter doesn't match what Robinhood reported?
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Amina Bah
•6 This is actually a common issue, especially with crypto or newer stocks. When you see "cost basis not reported to the IRS" on your 1099-B, you still need to enter your actual cost basis in FreeTaxUSA. The IRS requires you to report the correct information even if your broker didn't provide it to them. In FreeTaxUSA, when entering these transactions, there should be a checkbox or option to indicate "Basis not reported to the IRS." Make sure to check this and then enter your actual cost basis. You'll want to keep records of your purchase price in case of an audit.
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