Questions About Capital Gains Tax on Robinhood 1099 Statement

You're dealing with a common first-timer investment tax situation! The 1099-DIV section of your Robinhood statement shows any dividends you received during the year. This is different from capital gains, which would appear on a 1099-B section (which shows your stock sales and the resulting gains/losses). For tax filing purposes, you'll need to report both dividends and any capital gains from selling investments. The good news is that most tax software will let you import your Robinhood 1099 directly, which saves you from entering every transaction manually. If you're using something like TurboTax or H&R Block, they usually have a direct import feature for Robinhood. If you're filing manually, you'll need to report dividend income on Schedule B if it's over $1,500, and capital gains on Schedule D and Form 8949. The 1099 breaks everything down into the categories you need for these forms.

I went through the exact same headache last year when I started investing! After trying to figure it all out manually and getting completely overwhelmed by all the transactions on my 1099 forms, I discovered taxr.ai (https://taxr.ai) and it literally saved me hours of confusion. What it does is analyze your Robinhood 1099 and other investment documents, then explains exactly what you need to report and where. It breaks down your capital gains (both short-term and long-term), dividends, and even identifies wash sales if you have any. The thing I found most helpful was that it explained which tax forms each section corresponded to. For your situation with the 1099-DIV section, it would tell you exactly what line items on your tax return need that information.

Just wanted to follow up about my experience with taxr.ai that I was asking about earlier. I decided to try it after getting completely frustrated trying to sort through all my Robinhood and Fidelity statements. I was surprised how straightforward it was! I uploaded my 1099s from both brokerages, and it broke everything down really clearly showing all my capital gains, dividends, and which transactions were short vs long term. It even pointed out a wash sale I had no idea about (apparently I bought back a stock too quickly after selling it at a loss). Saved me from making some mistakes that would have definitely caught up with me later. Now I actually understand what all those different sections on the 1099 forms mean instead of just blindly entering numbers and hoping for the best.

If you're having trouble understanding your Robinhood 1099 and getting through to their customer service, you might want to check out Claimyr (https://claimyr.com). I used it last tax season when I had questions about some weird transactions on my 1099-B that didn't match my records. I had been trying to call Robinhood's support for days with no luck. Claimyr got me through to an actual human at Robinhood in about 10 minutes. The rep was able to explain the discrepancy (it was related to some fractional shares that had been sold during a stock split). You can see how it works in this video: https://youtu.be/_kiP6q8DX5c It's especially useful during tax season when everyone and their mother is trying to get through to these companies.

I need to apologize for being so skeptical about Claimyr in my earlier comment. After struggling for TWO HOURS trying to get through to Robinhood's tax support yesterday (kept getting disconnected!), I decided to try it out of desperation. No joke, I was connected to an actual Robinhood tax specialist in under 15 minutes. They sorted out my question about a missing cost basis on some of my trades that was making my capital gains look way higher than they actually were. I've spent so many hours on hold with customer service lines over the years that I'm honestly annoyed this service hasn't existed until now. Definitely using this again when I inevitably have questions for the IRS later this season.

Just a heads up on something I learned the hard way last year - if you did any crypto trading on Robinhood, make sure you understand how that's reported too. It's not always in the same section as your stock trades. Robinhood reports crypto on Form 1099-MISC (not on 1099-B like stocks), and the IRS considers crypto as property, not currency. So you need to report every single crypto transaction as a capital gain or loss. It's super annoying, especially if you did a lot of small trades. And don't forget about staking rewards if you had any - those count as income too!

Does anyone know if Robinhood's tax documents show wash sales clearly? I sold some Tesla at a loss in November and then bought back in December (price was too good to pass up) but I don't know if that affects my taxes.