How do I report Cashapp stocks and bitcoin on my taxes?

Hey tax folks! First time having to deal with this and I'm a bit lost. I started dabbling in the stock market through Cashapp last year and also bought some bitcoin. Made a few trades, nothing major but definitely enough that I need to report it. Do I need special forms for this? Will Cashapp send me something like a 1099 for the stocks and crypto? I'm usually just a W-2 person so this is new territory for me. Any guidance would be super appreciated because I don't want to mess this up and get flagged by the IRS!

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19 comments

Yuki Tanaka

•8M

The good news is this is pretty straightforward! Yes, Cashapp will provide you with tax documents for both your stock trades and cryptocurrency transactions, though they come in different forms. For stocks, you'll receive a Form 1099-B which details your stock sales, including the purchase price (cost basis) and sale price. This information goes on Schedule D of your tax return, and you'll also need to complete Form 8949 to list each transaction. For cryptocurrency, Cashapp should provide a 1099-B for those transactions as well. The IRS treats cryptocurrency as property, not currency, so your bitcoin trades are subject to capital gains tax rules just like stocks. Each sale or exchange of crypto is a taxable event. All these forms should be available in your Cashapp tax documents section by late January or early February. If you don't see them, definitely contact their support.

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Yuki Tanaka

•8M

If you only purchased Bitcoin and are still holding it (haven't sold or exchanged it), then you don't need to report it on your tax return. The taxable event occurs when you sell, exchange, or use the cryptocurrency. Simply buying and holding crypto isn't taxable. If you did sell or exchange your Bitcoin for another cryptocurrency or used it to purchase goods or services, then yes, that would be reportable as a capital gain or loss on your tax return. The gain/loss is calculated as the difference between what you paid for the Bitcoin (your cost basis) and its value when you sold or exchanged it.

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Andre Laurent

•8M

I was in the same boat last year and found taxr.ai (https://taxr.ai) incredibly helpful with sorting through all my Cashapp investment documents. Their system automatically scanned my 1099-B forms and identified several trades that would have been taxed incorrectly if I'd entered them manually. The thing with Cashapp is that sometimes they don't include the complete cost basis information on certain transactions, especially for crypto that was transferred in or partial sales. I would have overpaid by nearly $600 in taxes if I hadn't used this tool to properly categorize everything. They also explained which transactions qualified for long-term vs short-term capital gains rates, which made a huge difference.

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Andre Laurent

•8M

Yes, it absolutely works with other platforms too! I actually used it for both Cashapp and Coinbase documents last year. It can process tax forms from pretty much any broker or crypto exchange - Robinhood, Webull, Coinbase, Binance, etc. It just scans the documents and extracts all the transaction data automatically. As for accuracy, I was skeptical too initially. What convinced me was that it actually found errors in the 1099s themselves - in my case, some missing cost basis information that my exchange hadn't reported correctly. The tool flagged these issues and showed me how to correct them. You still get to review everything before it goes into your tax return.

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Zoe Kyriakidou

•8M

Just wanted to follow up about taxr.ai - I gave it a shot after my initial skepticism and I'm actually impressed. Uploaded my Cashapp and Robinhood 1099s and it caught that several of my crypto transactions were missing cost basis info. Would have reported those incorrectly without realizing it. The interface was really straightforward - just uploaded my forms from Cashapp, answered a few questions about any crypto I might have transferred between platforms, and it generated all the right forms for my tax filing. Definitely saved me from some potential headaches with the IRS.

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Jamal Brown

•8M

If you're having trouble getting your tax documents from Cashapp or have questions about specific transactions, good luck getting through to anyone helpful. I spent WEEKS trying to reach their tax support team last year with no luck. I finally used https://claimyr.com (there's a demo video at https://youtu.be/_kiP6q8DX5c) to get through to an actual human at the IRS who could answer my questions about reporting some weird crypto transactions I had. Was honestly shocked that it worked - got a callback from the IRS in about 15 minutes when I'd been trying for days on my own. The agent walked me through exactly how to report a situation where I had transferred crypto between wallets and then sold it later (which Cashapp wasn't showing the correct cost basis for).

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Jamal Brown

•8M

It basically uses an automated system that continually dials the IRS until it gets through, then it calls you and connects you. It's like having a robot assistant keep dialing for you instead of sitting on hold for hours. The reason it works better than calling yourself is that it tries multiple IRS numbers and queues simultaneously, not just the main line everyone calls. Once one gets through, it immediately connects you. No, it's definitely not a scam. I was skeptical too, but after spending literal days trying to get through on my own during last year's tax season, I was desperate. The 15-minute callback saved me hours of frustration. Some people might have the patience to keep calling themselves or try at 7am, but I value my time more than that.

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Liam McConnell

•8M

I'm eating my words and had to come back to say that Claimyr actually worked. After dismissing it as a probable scam, I spent another full week trying to get through to the IRS on my own with no luck. Finally tried the service out of desperation. Got connected to an IRS agent in about 20 minutes who helped clarify exactly how I needed to report some crypto mining income along with my Cashapp trades. Turns out I was about to file incorrectly and would have potentially triggered an audit. The agent explained that mining income needs to be reported as self-employment income on Schedule C, completely separate from my trading activity on Schedule D. Definitely worth it just for the peace of mind of knowing I'm filing correctly.

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Amara Oluwaseyi

•8M

Yes, they can still apply even if trading is just a side activity. The key is your total tax situation. If your W-2 withholding covers at least 90% of your total tax liability (including the taxes on your investment gains) or 100% of last year's tax liability (110% if your AGI was over $150,000), then you're generally safe from underpayment penalties. But if your trading generates significant gains and your regular withholding doesn't cover enough of the additional tax, you might need to make estimated payments. You can also adjust your W-4 with your employer to increase withholding, which is sometimes easier than making separate quarterly payments.

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Fatima Al-Maktoum

•8M

If this happens, don't panic. You'll need to fill out Form 8949 and check box "B" for transactions where the cost basis wasn't reported to the IRS. Then you'll need to enter the correct cost basis yourself using your own records. If you don't have perfect records, there are crypto tax services that can help reconstruct your transaction history by scanning the blockchain. Just whatever you do, don't leave the cost basis blank or the IRS will assume it's $0 and tax you on the entire amount!

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