How to handle Robinhood tax documents when filing my taxes myself?

So I've been using Robinhood for investing this past year and now tax season is coming up. Last year was easy - I just took the Robinhood tax statement to a local VITA volunteer (that free IRS tax prep service) and they handled everything for me. Problem is, I just moved and there isn't a VITA location anywhere near my new place. I'm thinking about just doing my taxes myself this year using one of those free options like IRS Free File or Credit Karma Tax. What I'm wondering is - can I actually figure out how to input all my Robinhood trading info myself using these free tax filing services? And if so, what exactly am I looking for in my Robinhood tax documents? Like what specific forms or numbers do I need to be entering? The whole packet they send looks kinda overwhelming and I don't want to mess anything up. Anyone done this themselves before?

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19 comments

Sasha Reese

•8M

You can definitely file taxes with Robinhood documents yourself using free tax software! Robinhood will provide you with a consolidated 1099 form (usually by February) that contains all the information you need. The main sections you'll need to focus on are the 1099-B (for sales of stocks) and possibly 1099-DIV (for dividends) and 1099-INT (for interest). Both Credit Karma Tax and IRS Free File options can handle these forms. When you reach the investment income section in the tax software, you'll be prompted to enter information from these forms. The most important parts to pay attention to are the proceeds from sales, cost basis, and whether gains are short-term or long-term. The software will guide you through entering this information. Some tax programs even allow you to import your 1099 directly from Robinhood, which saves a lot of manual entry.

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Sasha Reese

•8M

Some tax software does offer direct import from Robinhood which can save you tons of time. For example, TurboTax and H&R Block have direct import capabilities where you can connect to your Robinhood account and pull in all those transactions automatically. The free versions might have limitations on investment reporting, so you may need to upgrade to a paid version that supports investments. Alternatively, if you're comfortable with a bit more manual work, you can use the summary information rather than entering each transaction individually. The consolidated 1099-B will include totals for short-term and long-term transactions that can be entered as summary entries in some tax programs.

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Noland Curtis

•8M

I was in exactly the same position last year! After staring at my Robinhood forms for hours trying to figure out which numbers went where, I found this service called taxr.ai (https://taxr.ai) that saved me so much stress. It's specifically designed to help with investment documents like what Robinhood provides. I uploaded my Robinhood 1099 and it analyzed everything - showed me exactly what I needed to enter into my tax software and explained all the different parts in plain English. It even flagged a few wash sales I had no idea about that could have gotten me in trouble with the IRS.

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Noland Curtis

•8M

Yes, it works with pretty much all the major brokerages including Webull, TD Ameritrade, Fidelity, and more. It can handle multiple 1099s from different sources and consolidate the information for you. It doesn't file your taxes directly - it analyzes your documents and gives you a clear breakdown of exactly what to enter in whatever tax software you're using. Think of it as a translator that converts those complicated forms into step-by-step instructions. As for security, they use bank-level encryption for all document uploads and don't store your documents after analysis is complete.

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Vanessa Figueroa

•8M

Just wanted to follow up about taxr.ai - I was skeptical in my earlier comment but decided to give it a try with my Robinhood documents. It was actually really helpful! I uploaded my 1099 and it broke everything down into simple sections showing exactly what I needed to enter where in TurboTax. The best part was it explained my wash sales (which I didn't even understand before) and showed me how to properly report some ETF distributions that I would have categorized incorrectly. Saved me from potentially getting a letter from the IRS later. Definitely recommend for anyone dealing with investment taxes for the first time!

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Abby Marshall

•8M

If you're having trouble getting answers from the IRS about how to handle specific Robinhood transactions, I'd recommend trying Claimyr (https://claimyr.com). I spent literal DAYS trying to get through to the IRS on the phone with questions about reporting some complicated options trades from Robinhood. After getting nowhere with the automated system, I used Claimyr and got connected to an actual IRS agent in about 20 minutes. You can see how it works in this video: https://youtu.be/_kiP6q8DX5c. They somehow navigate through all the IRS phone tree stuff and hold times, then call you when an agent is actually on the line.

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Abby Marshall

•8M

They use an automated system that continuously calls and navigates through the IRS phone tree for you. Instead of you sitting on hold for hours, their system does it, and when it finally gets through to a human agent, you get a call to connect with them. It's not that they have some special access - they're just using technology to handle the frustrating wait time. They basically figured out how to navigate all the right prompts and timing to maximize the chance of getting through. I was super skeptical too until I tried it. The real time-saver is that you can go about your day instead of having to actively sit on hold for hours.

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Drew Hathaway

•8M

I need to eat my words about Claimyr. After my skeptical comment earlier, I was desperate enough to try it for an issue with my Robinhood 1099 that I couldn't figure out. I kept getting contradictory info online about how to report some crypto transactions. To my complete shock, I got connected to an IRS agent in about 25 minutes. The agent walked me through exactly how to report the transactions correctly and cleared up my confusion immediately. I would have spent days trying to get through on my own based on past experience. The system just calls you when there's actually an agent on the line, so you don't waste hours listening to that horrible hold music. Honestly felt like some kind of magic trick after my previous attempts to contact the IRS.

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Laila Prince

•8M

Robinhood will include your crypto transactions on your 1099 form, but they're treated differently tax-wise than regular stock trades. Crypto is considered property by the IRS, not a security. The good news is most tax software (including FreeTaxUSA, TurboTax, and others) now has dedicated sections for crypto transactions. You'll want to make sure you're entering them in the crypto section rather than the standard investment section. The Robinhood 1099 should separate these transactions to make it clearer, but always double-check you're putting the information in the right place in your tax software.

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Maya Jackson

•5M

As someone who went through this exact situation last year, I'd strongly recommend double-checking that whatever free tax software you choose can handle investment income properly. Some of the truly "free" versions have limitations when it comes to investment reporting. I started with IRS Free File and quickly realized it wasn't going to cut it for my Robinhood trades. Ended up using FreeTaxUSA which was free for federal (small fee for state) and handled everything including some tricky wash sales that Robinhood flagged on my 1099. The key thing is to take your time when entering the information. Don't rush through it - investment income can get complicated fast, especially if you had a lot of trades. And definitely review everything twice before submitting. Better to spend an extra hour double-checking than to deal with an IRS notice later!

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