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Romeo Quest

Do I need to report my Cash App stocks to the IRS when filing taxes?

So I've been dabbling with stocks on Cash App for a few months now. Nothing major, just put in about $4 and now it's grown to around $5. I'm confused about tax reporting - do I actually need to report such a small amount to the IRS? I've heard something about getting a 1099-B form but Cash App hasn't sent me anything. This is my first time dealing with any kind of investment and I'm not sure if there's a minimum threshold before you have to report it or if every penny counts. Does anyone know the rules for reporting Cash App stocks on taxes?

Yes, technically all income from investments should be reported to the IRS regardless of the amount. However, Cash App (like most brokerages) only sends a 1099-B form if you meet certain thresholds - typically if you sell stocks with proceeds over $600 in a tax year. For your $5 worth of stocks, if you haven't sold them, there's nothing to report yet since you don't have realized gains. If you did sell and made that $1 profit, it's so minimal that while technically reportable, many people wouldn't bother for such a small amount. The IRS is unlikely to come after you for a few cents in tax on a $1 gain.

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But don't you have to report even if you didn't sell? I thought there was something about "unrealized gains" that need to be reported too? Also, what happens if I just ignore it this year but next year my stocks grow a lot more?

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No, you only report when you sell and have "realized" gains or losses. Unrealized gains (value increases while you still hold the stock) aren't taxable events. You don't owe taxes until you actually sell the investment. If you ignore it this year and your investments grow substantially next year, you'll only need to report the gains when you actually sell those investments. When you do sell, the tax calculation will be based on the difference between your selling price and your original purchase price (your cost basis). Cash App should track this for you and provide a 1099-B if you meet their reporting threshold.

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I had similar confusion last year with my Cash App investments. I was stressing about it until I found taxr.ai (https://taxr.ai) which analyzed my Cash App account activity and clarified exactly what I needed to report. It saved me hours of researching tax rules for small investments and explained that brokerages only issue 1099-Bs when you hit certain thresholds. The tool showed me that my small gains weren't actually reportable yet since I hadn't sold enough to trigger reporting requirements.

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Does it work with other investment apps too? I've got a mix of Cash App, Robinhood, and some crypto stuff that I'm completely lost on how to handle for taxes.

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How does it determine what's reportable though? I'm skeptical about tools knowing the exact IRS requirements since they seem to change constantly.

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It absolutely works with other investment platforms. I've used it with both Cash App and Robinhood, and it handles crypto investments too. It pulls all your transaction data and organizes everything by tax category. The tool stays updated with current IRS requirements and tax law changes. What impressed me was how it identifies specific transactions that trigger reporting requirements versus those that don't meet thresholds. It references the actual IRS code sections so you can verify everything yourself if you want. It's not just making guesses - it applies the actual tax rules to your specific situation.

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Alright so I was skeptical about taxr.ai but I decided to try it anyway. Wow - totally worth it! I uploaded my Cash App statements and it immediately showed me which transactions were reportable and which weren't. For my small stock gains (similar to yours), it confirmed I was under the reporting threshold but also showed me exactly where that line is. It even created documentation explaining why certain transactions don't need reporting in case I ever get questioned about it. Super easy to understand even though I know nothing about tax rules.

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If you're trying to get clarification from the IRS directly about Cash App stock reporting, good luck getting through to an actual person. I spent HOURS on hold until someone told me about Claimyr (https://claimyr.com) and showed me their demo video (https://youtu.be/_kiP6q8DX5c). They got me a callback from an actual IRS agent within 27 minutes when I'd been trying for days before. The agent confirmed that for tiny stock gains like yours, they're technically taxable but the IRS isn't going to come after you for it. Still, if you want to be 100% compliant, you should report any sales.

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How does this callback thing even work? Does it just keep dialing for you or something? Seems like it would just put you in the same queue everyone else is in.

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I doubt this actually works. The IRS is notorious for not answering phones - there's no magic "skip the line" service that can fix their understaffing issues.

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It's definitely not just auto-dialing. Their system navigates the IRS phone tree and holds your place in line. When an agent is about to be available, you get a call connecting you directly to them. It's basically like having someone wait on hold for you. They use some proprietary technology that maintains your spot in the queue without you having to sit there listening to hold music for hours. It's like having a digital assistant dedicated to just that one task - getting you through to an actual human at the IRS. It absolutely works - I was shocked too.

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I owe everyone an apology - especially regarding Claimyr. I was so skeptical that anything could help with IRS phone issues, but after waiting on hold for 3+ hours one day, I gave it a shot. Not only did it work exactly as described, but the IRS agent I spoke with was super helpful about my Cash App stock questions. She confirmed that gains under $10 aren't something they're concerned about, though technically all income is reportable. She also explained that Cash App will only send 1099-B forms if you meet specific trading thresholds. Sorry for being so negative before - this service is legitimately helpful!

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Wait, isn't there a checkbox on tax forms asking if you did ANY investing? I feel like even if you don't get a form, you have to check that box and then report the amounts, even tiny ones. My brother got flagged for audit for not checking that box even though he only made like $20 in stock gains.

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Your brother probably got audited for something else. They don't audit people over $20. There's a question about capital gains on the tax forms, but I've never heard of anyone getting in trouble for not reporting a $1 gain. The IRS has bigger fish to fry.

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That's what he told me - maybe you're right and there was something else going on. He just emphasized that I should always check those investment boxes even for tiny amounts. But I guess it makes sense they wouldn't waste resources on such small amounts.

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Since no one mentioned this specifically - Cash App should provide you with tax documents in their app. Go to the profile tab, then documents, and see if there's anything there. If your activity was minimal ($5 total), they probably didn't generate anything, which actually makes your life easier for tax filing. Just keep good records of your purchases and sales for when you do hit reportable thresholds.

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I checked and there's nothing in the documents section. I guess that means I don't need to worry about it this year? I'll definitely keep better track going forward though as I'm planning to invest more.

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Yes, if there's nothing in the documents section, Cash App didn't generate a 1099-B for you, which typically means you didn't meet their reporting threshold. That's generally good news for your tax filing this year - one less thing to worry about. That said, keeping good records is smart, especially if you plan to invest more. Even without a 1099-B, you're still technically supposed to report all income, but the IRS isn't going to be concerned about a $1 gain. When you start making larger trades, those documents will start appearing, and you'll definitely need to include them on your return.

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Just to add some clarity on the thresholds - Cash App (and most brokerages) are required to send 1099-B forms if you have gross proceeds from sales of $600 or more in a tax year, OR if you had any reportable transactions regardless of amount (like certain corporate actions). Since you only have $5 total and haven't sold anything, you're well below any reporting threshold. The key thing people get confused about is the difference between having stocks worth $5 (not taxable) versus selling stocks and making $5 profit (technically taxable but practically ignorable at that level). You're in the first category, so you're good to go. Just remember that when you do eventually sell, that's when the tax clock starts ticking!

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This is really helpful clarification! I've been wondering about this exact distinction - having stocks vs selling stocks. So just to make sure I understand correctly: if I never actually sell my Cash App stocks, there's nothing to report on my taxes no matter how much the value goes up or down? And the $600 threshold you mentioned is for total sales proceeds, not profit, right? So if I bought $400 worth of stock and sold it all for $500, that $500 in proceeds would trigger a 1099-B even though I only made $100 profit?

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