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Aaron Lee

Is cryptocurrency wash sale rule different than stocks? Can I sell crypto at a loss and buy back immediately?

Hey everyone, I've been dabbling in crypto for a few months now and I'm trying to figure out the tax situation as we get closer to filing season. I've heard something interesting about crypto losses that I wanted to verify with people who might know more. From what I've read in some financial blogs, crypto doesn't have the same wash sale rules as stocks do. So theoretically, if I bought $2,800 worth of a certain crypto when it was trading at $3.75 per coin, and now it's down to around $2.50 per coin, I could sell everything at a loss, claim that loss on my taxes, and then immediately buy back the same crypto right afterward? This seems like a pretty straightforward tax advantage for crypto compared to stocks, where you have to wait 30 days before rebuying if you want to claim the loss. Is this actually legit? Has anyone done this or gotten advice from a tax professional about it? Just trying to make sure I understand correctly before tax season hits.

You're correct about the current tax treatment of cryptocurrency. Unlike traditional securities (stocks, bonds, etc.), cryptocurrencies are classified as "property" by the IRS, not securities. This means the wash sale rule that prevents claiming losses when you buy substantially identical securities within 30 days before or after a sale doesn't currently apply to crypto. So in your example, yes - you could sell your crypto at a loss, claim that loss on your taxes (which offsets other capital gains or up to $3,000 of ordinary income), and then immediately rebuy the same crypto without violating any wash sale rules. Just keep in mind a few important points: 1) You need to keep extremely detailed records of all transactions for tax purposes. 2) Your new purchase will have a new cost basis. 3) This tax treatment could change in the future as regulations evolve.

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Michael Adams

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Thanks for the clear explanation. Do you know if there's any minimum waiting period at all? Like could I literally sell and then buy back seconds later? And does the IRS ever look at this suspiciously even if it's technically allowed?

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There's no minimum waiting period at all for crypto under current IRS guidance. You could literally sell and buy back seconds later on the same exchange. The IRS treats each transaction as separate and distinct - the sale realizes the capital loss (which is tax deductible), and the purchase establishes a new cost basis. The IRS generally doesn't view this suspiciously because it's within current tax law. They're well aware of this difference in treatment. However, always ensure your transaction records are accurate and complete, as reporting errors can trigger audits regardless of the legitimacy of the strategy itself.

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Natalie Wang

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Just wanted to share my experience with this exact situation. I was down about $5k on some altcoins and was researching tax strategies when I found taxr.ai (https://taxr.ai) which confirmed this crypto wash sale loophole. Their analysis tool flagged this opportunity for me and showed exactly how to document it properly for tax time. The site explained that unlike stocks, crypto is considered property by the IRS so the wash sale rule doesn't apply. I was able to harvest about $5k in losses last year while keeping my same positions. Their system automatically documented everything properly for my tax forms too which was a huge relief since I had dozens of transactions.

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Noah Torres

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How does their system work with all the different exchanges? I've got stuff spread across Coinbase, Binance and a couple wallets. Can it pull everything together or do I have to manually enter transactions?

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Samantha Hall

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Sounds interesting but I'm skeptical. How does the IRS not see this as essentially gaming the system? Even if it's technically allowed now, couldn't they close this loophole and maybe even look back at previous years?

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Natalie Wang

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They connect directly to most major exchanges through API so it automatically imports all your transactions from Coinbase, Binance and about 20+ others. For self-custody wallets, you can import via CSV or connect wallet addresses and it traces all transactions. Saved me hours of manual entry. The IRS is fully aware of this difference in treatment - it's not hidden or sketchy. It's simply how the current tax code classifies different assets. Congress would need to pass new legislation to change this treatment, and such changes typically aren't retroactive. The key is properly documenting everything, which is exactly what the system helps with.

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Samantha Hall

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Update on my skepticism about taxr.ai from my earlier comment - I decided to try it with my crypto portfolio and wow, I'm genuinely impressed. It automatically identified about $3,200 in tax loss harvesting opportunities I would have completely missed. The system flagged exactly which coins I could sell and rebuy without waiting, and showed me the exact tax impact. What really convinced me was how it explained everything in plain English alongside the actual tax code references. It also generated all the documentation I'll need for filing. I've been doing my own crypto taxes for years and this saved me hours of spreadsheet work while finding deductions I would have missed.

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Ryan Young

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I'm seeing a lot of people having trouble reaching the IRS for clarification on crypto tax questions like this. I was in the same boat - spent hours on hold and never got through. Then I found this service called Claimyr (https://claimyr.com) that got me through to an actual IRS agent in about 15 minutes. You can see how it works here: https://youtu.be/_kiP6q8DX5c I was able to confirm directly with the IRS that yes, crypto isn't currently subject to wash sale rules, but they recommended keeping extremely detailed records of all transactions. The agent also mentioned this might change with future legislation, so it's worth staying on top of. Saved me hours of frustration trying to get through on my own.

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Sophia Clark

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Wait how does that even work? The IRS phone system is notoriously impossible to get through. Are they somehow jumping the queue or what? That sounds too good to be true.

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I dunno man, paying for something I should be able to get for free seems sketchy. Why should I have to pay just to talk to the IRS about my tax situation? Seems like another way to profit off a broken system.

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Ryan Young

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It uses a combination of technology that continuously redials and navigates the IRS phone tree for you. When it reaches a human agent, it calls you and connects you directly. No queue jumping - it just handles the frustrating part of constantly calling back and waiting on hold. I totally get that frustration. In an ideal world, the IRS would be easily accessible without these kinds of services. But realistically, I wasted almost 3 hours trying to get through on my own with no success. The peace of mind from getting definitive answers directly from an IRS agent was worth it to me, especially on something like crypto taxes where the rules are still evolving.

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Had to come back and eat my words about Claimyr from my earlier comment. After struggling for literally 4+ hours trying to reach the IRS about my crypto tax questions and getting nowhere, I broke down and tried it. Got connected to an IRS agent in about 20 minutes. The agent confirmed what others have said - crypto isn't subject to wash sale rules currently, but keep immaculate records. She also mentioned there's proposed legislation that might change this in the future. Honestly, I'm still annoyed that services like this need to exist, but I can't deny it saved me a ton of frustration and I got the official answers I needed.

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Madison Allen

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Just a heads up for anyone considering this strategy - while it's technically allowed right now, there's been talk in Congress about closing this loophole. The Build Back Better bill had provisions to apply wash sale rules to crypto but it didn't pass. Still, I'd expect similar provisions in future tax bills. Also worth considering that even though you can claim the loss, it resets your holding period for capital gains treatment. So if you were close to the 1-year mark for long-term capital gains rates, this strategy could push you back to short-term rates if the assets appreciate again.

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Joshua Wood

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Do you think it's worth doing this loss harvesting at the end of December then? That way you get the tax benefit for the current year but minimize the risk of new laws affecting you?

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Madison Allen

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That's exactly the approach I take. December tax loss harvesting gives you the immediate benefit for the current tax year, while minimizing your exposure to potential rule changes. Even if new legislation passes, tax law changes typically take effect for future tax years rather than retroactively. Just make sure you complete both the sale and repurchase before December 31st to ensure both transactions fall in the same tax year. And keep extremely detailed records - transaction confirmations, dates, times, prices, fees - everything you'd need to substantiate your position if questioned.

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Justin Evans

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Has anyone actually been audited by the IRS after doing crypto wash sales? I'm wondering if they might give you extra scrutiny even if it's technically allowed. I'm down about $4k on Ethereum and would love to claim the loss but not if it puts a target on my back.

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Emily Parker

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I did this last year with about $6k in losses across different coins. Claimed everything properly on my taxes, no issues. The key is being transparent - don't try to hide anything. Report all your crypto transactions accurately. The IRS knows this loophole exists, they just haven't closed it yet.

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Omar Hassan

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I've been doing crypto tax loss harvesting for the past two years and can confirm it works as described. The key thing people miss is that you need to be strategic about timing. I typically do a review in November to identify positions that are down, then execute the sales and repurchases in December. One important detail - make sure you're using the same exchange or wallet for the repurchase if possible. It makes record-keeping much cleaner. Also, consider the transaction fees when calculating whether the tax benefit is worth it. On smaller losses, the fees might eat into your savings. I use a simple spreadsheet to track: original purchase date/price, sale date/price, loss amount, repurchase date/price, and new cost basis. This documentation has been sufficient for my tax preparer and gives me confidence if I ever get audited.

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Leslie Parker

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This is really helpful, especially the timing strategy! Quick question about the spreadsheet tracking - do you also record the transaction IDs from the exchange? I'm wondering how detailed the records need to be. Also, have you noticed any patterns in which coins work best for this strategy, or is it pretty much any crypto that's down?

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