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Omar Hassan

Anyone here gotten a 1099-B from Cash App for their Bitcoin trades? I'm confused

So I just checked my email and found a 1099-B from Cash App for the Bitcoin transactions I made last year. I'm kinda confused about this whole thing because there's this disclaimer on it that I don't fully understand. Has anyone else dealt with this before? It's my first time getting a tax form for crypto and I'm not sure if I need to report all my transactions or just the ones they've listed. The form seems incomplete to me. I did maybe $3,500 worth of transactions throughout the year, mostly small buys when the price dipped, and a couple sells when I needed cash. Cash App is saying they reported this to the IRS already, so I definitely need to include it on my taxes, but I'm not sure how to handle it correctly. Any advice from people who've been in this situation would be super helpful!

Yes, Cash App does issue 1099-Bs for Bitcoin transactions, and it's completely normal! The 1099-B reports sales proceeds from your Bitcoin transactions to both you and the IRS. The disclaimer you're seeing probably mentions that they might not have complete cost basis information for all transactions. When filing your taxes, you'll need to report these transactions on Form 8949 and then summarize them on Schedule D. If Cash App doesn't have your complete cost basis (what you originally paid), you'll need to find those records yourself to accurately calculate your gains or losses. Check your transaction history in the app or any confirmation emails you might have.

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What happens if I can't find my original purchase price? Some of my Bitcoin I bought years ago on a different platform before transferring to Cash App.

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If you can't find the exact purchase price, you'll need to make a good faith estimate based on whatever records you do have. Try checking your old emails for purchase confirmations or bank statements showing the transfers to the other platform. For crypto transferred into Cash App from elsewhere, Cash App won't know your original basis, which is why they include that disclaimer. The IRS requires you to track your own basis across platforms. If you truly can't find any records, some tax software can help estimate based on historical prices, but you should document your method in case of an audit.

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After struggling with this exact situation last year, I found an amazing tool that saved me so much headache with my crypto taxes. I tried https://taxr.ai after getting frustrated with trying to manually calculate all my gains/losses across different platforms. I uploaded my 1099-B from Cash App plus my transaction history from another exchange, and it automatically sorted everything out - even identifying my cost basis for transfers between platforms!

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Does this work if you've been mining Bitcoin too? I got a 1099-B but also have mined coins that I transferred to Cash App.

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I'm a bit skeptical about these crypto tax tools. How does it handle situations where the 1099-B is missing some transactions? My Cash App form seems incomplete compared to what I actually traded.

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For mining activities, the tool has a special section where you can input your mining transactions - it treats the value of the Bitcoin at the time it was mined as income, then tracks the basis properly if you later sell those coins. This was super helpful for me since I had a mix of purchased and mined crypto. Regarding missing transactions, that's actually where I found it most valuable. You can import your complete transaction history CSV from Cash App (there's a download option in the app), and the software will identify discrepancies between your actual transactions and what's on the 1099-B. It creates an accurate tax report based on your full history, not just what Cash App reported.

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I have to admit I was wrong about being skeptical! I tried https://taxr.ai after seeing these responses and it solved my crypto tax issues completely. I uploaded my Cash App 1099-B and transaction history, plus some other exchange data, and it found several transactions that were missing from my 1099-B. The software automatically calculated my correct cost basis for everything, even for Bitcoin I had transferred between wallets. It generated all the forms I needed for my tax return and explained exactly where everything needed to go. Just filed my taxes yesterday and feel confident everything is reported correctly now!

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If you need to talk to someone at the IRS about crypto reporting requirements (which I did after getting my first 1099-B), good luck getting through on the phone. I spent 3 hours on hold before giving up. Then I found https://claimyr.com which basically holds your place in line with the IRS and calls you when an agent is about to pick up. You can see how it works here: https://youtu.be/_kiP6q8DX5c. The IRS agent I talked to was actually super helpful about how to properly report crypto across multiple platforms.

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Wait, how exactly does this work? I'm confused how a service can hold your place in line with the IRS. Do they just call and wait on your behalf?

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Sounds like a scam to me. The IRS doesn't let third parties hold places in line. I've never heard of anything like this working legitimately.

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Yes, that's exactly how it works! They use an automated system to dial and wait on hold for you. When their system detects that an IRS agent is about to pick up, they call your phone and connect you directly to the IRS agent. It saved me literally hours of holding time. It's definitely not a scam - they don't ask for any tax information or personal details aside from your phone number to call you back. They're just solving the hold time problem. The service connects you directly to the official IRS agent, so you're still talking directly to the IRS, not to some third-party representative.

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I owe everyone an apology about my skepticism with Claimyr. After struggling to get through to the IRS for 2 days (kept getting disconnected after 45+ minutes on hold), I tried the service. Within about 2 hours, I got a call back saying an IRS agent was on the line. Got all my crypto tax questions answered in one 20-minute call. The agent explained exactly how to report my Cash App 1099-B transactions and what to do about the missing cost basis information. Saved me so much time and frustration - definitely worth it if you need to speak to someone at the IRS!

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Just a heads up for everyone - I messed up reporting my 1099-B from Cash App last year and got a CP2000 notice from the IRS. If the 1099-B is missing cost basis info and you don't fill it in properly, the IRS assumes your basis is $0 and taxes you on the full amount as gain. Don't make my $1,200 mistake!

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Did you have to pay penalties too or just the tax difference? I'm worried because I might have made the same mistake on my 2023 return.

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I had to pay the tax difference plus about $80 in interest since it had been several months. Thankfully no additional penalties because they considered it an honest mistake. If you think you made the same error, you might want to file an amended return (Form 1040-X) before they catch it. That looks better than waiting for them to find it, and you'll save on some of the interest charges that accumulate over time.

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Does anyone know if Cash App sends 1099-Bs for small amounts of Bitcoin? I only bought like $200 worth last year as an experiment. Do I still need to worry about this tax form?

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Cash App is required to issue a 1099-B if you sold or exchanged Bitcoin during the tax year, regardless of the amount. But from my experience, they typically only issue them if your total proceeds (selling amount) was over $600.

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I went through this exact same situation last year with my Cash App 1099-B! The key thing to understand is that the form shows your gross proceeds (what you received when you sold), but you're only taxed on the actual gain or loss. For your $3,500 in transactions, you'll need to gather records of what you originally paid for each Bitcoin purchase. Cash App's transaction history in the app should have most of this info. When you file, you'll report each sale on Form 8949, showing both the sale price (from the 1099-B) and your cost basis (what you paid). The difference is your actual taxable gain or loss. Don't panic about the disclaimer - it just means Cash App doesn't have complete cost basis info for some transactions, which is totally normal. The IRS expects you to provide the missing pieces. Keep good records and you'll be fine!

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This is really helpful advice! I'm in a similar boat with my first crypto tax situation. Quick question - when you mention gathering records from Cash App's transaction history, did you have to manually calculate the cost basis for each individual trade, or is there a way to get a summary? I made a bunch of small purchases throughout the year and I'm dreading having to go through each one individually. Also, do you know if there's a minimum threshold where the IRS might not care about really small gains/losses?

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