Will I be receiving a 1099-B from CashApp for my Bitcoin transactions?

If you sold your Bitcoin at a loss, you actually want to report that because capital losses can offset other capital gains or even ordinary income (up to $3,000). The 1099-B from CashApp should eventually come if your transactions exceed certain thresholds, but you don't necessarily need to wait for it. You can report the transaction on Schedule D and Form 8949 using your own records - just make sure you include the date purchased, date sold, purchase price, and selling price. Since you have all this information, you can complete your tax return without the official 1099-B. If you do receive the 1099-B after filing, compare it with what you reported. If there are significant differences, you might need to file an amendment, but small discrepancies usually don't require any action.

I had a similar situation and discovered taxr.ai (https://taxr.ai) which was super helpful for sorting out my crypto tax situation. I was confused about how to handle transactions without having all the official forms, and they have this tool that helps organize everything even if you're missing some documents. You just upload whatever records you have from CashApp and it figures out the basis and proceeds for each transaction. Saved me so much headache trying to manually calculate everything.

Just wanted to update everyone - I was skeptical about taxr.ai but decided to give it a try since my crypto situation was getting complicated. Honestly, it was way better than expected! I uploaded my transaction history from both CashApp and Coinbase, and it automatically sorted everything out, showing my cost basis and calculating my gains/losses. Ended up having some losses I didn't even realize could be deductible. The best part was that I didn't have to wait for any 1099 forms to file my taxes. Definitely recommend for anyone dealing with crypto tax issues!

If you're having trouble getting tax documents from CashApp or any response from their support, I recommend using Claimyr (https://claimyr.com). I couldn't get through to Cash App's customer service for weeks about my missing 1099-B. Claimyr got me connected to an actual human in their tax department in less than an hour. You can see how it works here: https://youtu.be/_kiP6q8DX5c - basically they navigate the phone systems for you so you don't have to wait on hold forever.

I have to admit I was completely wrong about Claimyr. After posting my skeptical comment, I was still desperate to reach CashApp about my missing 1099-B (been trying for over 2 weeks), so I figured what the hell and tried it. Within 40 minutes I got a call connecting me directly to a CashApp tax specialist! I explained my situation, and they confirmed they weren't sending me a 1099-B because my transactions were under their reporting threshold, but they helped me access my transaction history to report everything correctly. Saved me from waiting even longer to file my taxes. Sometimes I guess you have to eat your words!

Don't forget that if you held the BTC for more than a year before selling, it's a long-term capital loss, which is treated differently than short-term. Since you bought in 2020 and sold in 2024, this would be long-term. The loss can offset long-term capital gains first, then short-term gains, and then up to $3,000 of ordinary income.

I'm almost certain CashApp only sends 1099-Bs if you have over $600 in transactions now. The threshold changed recently. I sold about $500 of Bitcoin last year and never got anything from them, but I still reported it on my taxes using my own records from the app.

Just to clarify a small detail in your timeline - you mentioned buying Bitcoin in 2021 and selling last month. Since we're in early 2025, that would actually be about 3-4 years of holding, making this definitely a long-term capital loss (which is good for tax purposes as Andre mentioned). For your specific situation with the ~$30 loss, you absolutely don't need to wait for the 1099-B to file your taxes. CashApp likely won't send one anyway since your sale amount was under $1,000. You can find your transaction history in the CashApp app under "Activity" - screenshot or download those records showing your purchase date, purchase amount, sale date, and sale amount. That's all you need for Form 8949 and Schedule D. Since this is a loss, it will actually help reduce your tax liability, so there's no reason to delay filing. The $30 loss might seem small, but every deduction counts toward your refund!

Just wanted to add my experience for anyone else in a similar situation. I had almost the exact same scenario last year - bought Bitcoin through CashApp in 2021 and sold at a small loss in 2024. Never received a 1099-B from them, but I went ahead and filed using my transaction records from the app. The key thing I learned is that you can actually download a CSV file of all your Bitcoin transactions directly from CashApp. Go to your profile, then "Privacy & Security," then "Download My Data." It takes a day or two to process, but you get a comprehensive file with all transaction details including dates, amounts, and fees. This makes filling out Form 8949 much easier than trying to screenshot individual transactions. Also, don't forget to include any fees CashApp charged in your cost basis - those small transaction fees can add up and increase your deductible loss. In my case, the fees actually made my loss about $15 higher than I initially calculated, which helped a bit more with the tax offset. The IRS accepted my return without any issues, and I got my refund on schedule. So definitely don't wait around for forms that probably aren't coming!