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Elijah Knight

Do I need to report Cash App stocks to the IRS for tax purposes?

So I've been dabbling with Cash App investments, literally just tiny amounts. I put in around $4 last year and now it's worth about $5 (woo, big money, I know lol). I'm confused about tax reporting - do I actually need to report this dollar gain to the IRS? I've heard something about a 1099-B form that should come from investment platforms, but Cash App hasn't sent me anything. Not trying to hide income or whatever, just wondering if there's some minimum threshold before you have to report stock gains or if I'm supposed to be getting tax forms for this tiny amount. Anyone know how this works with Cash App specifically?

Tax professional here! For stock sales, the reporting rules are pretty straightforward. Brokers (including Cash App) are only required to issue a 1099-B if you have sales proceeds exceeding $600 in a tax year. With your $5 situation, you're well below that threshold, which explains why you haven't received any forms. However, technically speaking, ALL capital gains are reportable on your tax return regardless of whether you receive a form. Your $1 gain would be reported on Schedule D and Form 8949. That said, the IRS isn't likely to come after you for a $1 gain that wasn't reported. If you want to be 100% compliant, you can report it. The tax on $1 would be negligible or possibly zero depending on your tax bracket. But most tax software will charge you extra to file with investment income, which would cost more than any potential tax you'd owe.

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Wait so is there a minimum amount before we need to report? Like if I made $20 in stocks do I need to file that? What if I lost money instead of gaining?

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There is no minimum threshold for reporting capital gains - technically all gains should be reported regardless of amount. If you made $20 in stocks, yes, that should be reported on your tax return using Schedule D and Form 8949. If you lost money instead of gaining, those losses can also be reported and may be tax-beneficial. Capital losses can offset capital gains, and if your losses exceed your gains, you can deduct up to $3,000 of those losses against your ordinary income. Any remaining losses can be carried forward to future tax years.

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I've been using Cash App for stock trading for about 2 years and was also confused about how to handle the taxes. After a lot of searching, I found this amazing tool called taxr.ai (https://taxr.ai) that helped me figure out exactly what I needed to report. You upload your documents or screenshots of your transactions, and it tells you exactly what goes where on your tax forms. For small amounts like yours, they confirmed I wouldn't get a 1099-B but still helped me report it correctly. The nice thing is it handles all sorts of investment platforms including Cash App, which many tax services don't specifically address. It saved me a ton of headaches trying to figure out if I was doing it right.

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Does it help with crypto too? Cash App let's you buy Bitcoin and I'm completely lost on how to report that stuff.

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How does it work with the actual tax filing though? Does it integrate with TurboTax or do you have to manually enter everything it tells you?

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Yes, it absolutely helps with crypto reporting too! It can handle Bitcoin transactions from Cash App and gives you the proper tax treatment for crypto, which follows different rules than regular stocks sometimes. For tax filing integration, it provides you with the completed forms and exact figures you need. You can manually enter these into any tax software like TurboTax, H&R Block, or others. It basically does the complicated calculation part so you just need to plug in the final numbers. It saved me from upgrading to the expensive "premium" versions of those tax programs.

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Just wanted to follow up - I tried taxr.ai for my Cash App Bitcoin and stock transactions and it was super helpful! I had about $75 in gains that I wouldn't have known how to report properly. The system showed me exactly what I needed to enter in my tax software and even explained the different tax rates for my short-term vs long-term holdings. Definitely worth using if you have any investment income, even small amounts.

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Lots of good advice here already, but FYI - if you ever have more complex tax situations or questions about your Cash App investments, trying to get answers from the IRS directly can be nearly impossible. I spent hours on hold trying to clarify some investment tax rules. Eventually I found Claimyr (https://claimyr.com) and watched their demo (https://youtu.be/_kiP6q8DX5c) - basically they get you through to an actual IRS agent by navigating their phone system for you. I was able to speak with someone who clarified exactly how to handle my Cash App investments, including some fractional shares I wasn't sure about. Saved me hours of waiting on hold and the stress of wondering if I was doing it right.

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How does that even work? Seems sketchy that they could somehow get you through faster than calling yourself.

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Yeah right. Nobody gets through to the IRS. I've tried calling for 3 years straight with questions about my 1099 reporting and never once reached a human. This sounds like a scam to me.

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It's actually pretty straightforward how it works. They use an automated system that navigates the IRS phone tree and waits on hold for you. When they reach a real person, they call you and connect you directly to that agent. You're not skipping the line - they're just handling the hold time for you. I was skeptical too, but it's completely legitimate. The IRS phone system is designed to handle millions of calls, but their staffing hasn't kept up with demand. What Claimyr does is wait through that hold time (which can be 2-3 hours) so you don't have to sit there with your phone to your ear the whole time.

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Okay I feel dumb but I need to come back and apologize. I tried Claimyr after posting that skeptical comment because I was desperate about a tax question. It actually worked exactly as described. Got a call back in about 45 minutes and was connected to an IRS agent who answered my questions about reporting some small stock gains like the OP mentioned. Sorry for being so negative before - just been burned by too many services promising to help with tax stuff.

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For what it's worth, I've been using Cash App for investments for a while, and they DO send 1099-Bs but only if you sell more than $600 worth of investments in a year. The app itself keeps track of your gains/losses though. If you go to your investing tab and click on the activity section, you can see your complete history and could calculate the gain yourself if needed.

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Thanks! I just checked and found that section in the app. It does show my tiny gains right there. So if I'm under the $600 threshold I guess I'm technically supposed to report it but it's such a tiny amount maybe it doesn't matter much?

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Technically, yes - all capital gains should be reported regardless of amount. But realistically, for a $1 gain, the tax would be literally pennies even at the highest tax rates. Most tax professionals would tell you that while you should report everything by the letter of the law, the IRS isn't going to come after you for such a small amount. If you're filing taxes through software anyway, you might want to include it for peace of mind. But if reporting it means you need to pay extra for a premium tax filing tier, it's probably not worth the extra cost just to report a $1 gain.

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Has anyone noticed that Cash App takes forever to send tax documents? Last year my 1099 didn't arrive until late March even though they're supposed to send them by Feb 15. Just wondering if that's common.

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That happened to me too! I had to file an extension because my Cash App 1099 came so late. This year I'm just going to download my transactions history and calculate everything myself instead of waiting for their forms.

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I'm dealing with a similar situation - made about $12 in gains from Cash App stocks last year and wasn't sure about reporting it. After reading through all these responses, I think I'm going to go ahead and report it just to be safe, even though it's such a tiny amount. One thing I found helpful was logging into Cash App and going to the "Taxes" section under settings - they actually have a downloadable CSV file with all your investment activity that makes it easier to calculate your gains/losses. For anyone in the same boat with small amounts, this might be easier than trying to manually track everything from the activity feed. Thanks everyone for the detailed explanations about the $600 threshold for 1099-Bs - that clears up a lot of confusion I had!

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That's a smart approach! I didn't know about the downloadable CSV file in the Taxes section - that sounds way easier than trying to piece everything together from the activity feed. I'm in a similar boat with small gains (around $8) and was going back and forth on whether to report it. Your point about doing it just to be safe makes sense, especially since the actual tax on such small amounts would be practically nothing anyway. Thanks for sharing that tip about the CSV download!

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