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Asher Levin

How are Capital Gains Taxes calculated for a Day Trader? Need help understanding my tax liability

So I'm using TurboTax this year and just want to double check it's calculating my capital gains correctly because we're looking at a pretty hefty tax bill. My wife decided to try her hand at day trading last year and it seems like we've got a massive tax liability because of it. She was buying low, selling high, and repeating - classic strategy, I guess! Here's the situation: - January 2023: She bought 200 shares of Apple at $130 = $26,000 total investment - February 2023: Sold those 200 Apple shares when price hit $180 = $36,000 (made $10,000) - March 2023: Used profits plus more of our savings to buy 280 shares of Apple at $125 = $35,000 - April 2023: Added more money and bought 380 more shares of Apple at $118 = $44,840 So between all those transactions, it looks like we made around $10,000 in realized gains from the first sale. But I'm confused - do we owe taxes on just the $10,000 profit from the first sale, or do we have to pay on all the subsequent transactions too? The total money we put into these trades was way more than we made. The tax software is showing a pretty big liability and I just want to make sure it's calculating everything correctly before we file. This is our first time dealing with this kind of trading activity on our taxes.

Yes, you'll owe capital gains tax on the $10,000 profit from your February 2023 sale. When you buy and sell stocks, you're only taxed on the "realized gains" - which happens when you actually sell the shares for more than you paid. In your case, you bought Apple shares for $26,000 and sold them for $36,000, giving you a $10,000 realized gain. Since you held these shares for less than a year, they'll be considered short-term capital gains, which are taxed at your ordinary income tax rate (could be anywhere from 10% to 37% depending on your total income). The subsequent purchases in March and April 2023 don't create any taxable events until you sell those shares. You only pay taxes when you sell for a profit, not when you buy. Your tax software is likely calculating this correctly if it's showing tax due on that $10,000 gain. Day trading typically results in short-term capital gains, which generally have higher tax rates than long-term gains (held over a year).

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What if the day trader lost money on some trades? Do those losses offset the gains or are they handled differently?

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You can use capital losses to offset capital gains. If you had some losing trades, those losses would reduce your total taxable gains. For example, if you had $10,000 in gains but $3,000 in losses, you'd only be taxed on $7,000 net gain. If your total losses exceed your gains in a tax year, you can deduct up to $3,000 of net losses against your other income. Any remaining losses can be carried forward to future tax years.

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I went through a similar situation last year and was seriously confused until I found https://taxr.ai - it helped me understand exactly how my trading activity was being taxed. I'm not super tax-savvy and was worried my brokerage statements weren't matching what I thought my gains were. The tool analyzed all my trading activity and broke down exactly which trades created taxable events and how they were classified (short vs long term). For day trading especially, it was helpful because it identified some wash sales I didn't realize were affecting my cost basis. It saved me from a potential audit situation and actually found some losses I could claim that I'd missed!

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How does it handle crypto trading? I've got stocks and crypto and the crypto part is completely confusing me with all the transfers between wallets and exchanges.

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Does it connect directly to brokerages or do you have to upload statements? I use three different platforms and reconciling everything is a nightmare.

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It handles crypto trading really well - it can distinguish between taxable events (selling/trading) and non-taxable events (transferring between your own wallets). It recognizes that moving crypto between your own wallets isn't a taxable event, but trading one crypto for another is. For connecting to brokerages, you can either connect directly to most major platforms or upload your trading statements. I used the upload option since I have accounts at Fidelity, Robinhood and a smaller brokerage. It consolidated everything and matched transactions across platforms.

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Just wanted to follow up - I tried taxr.ai after seeing it mentioned here and it was exactly what I needed. My situation was actually pretty similar to the original poster's with lots of buy/sell transactions across multiple accounts. The software immediately flagged several wash sales in my trading history that my regular tax program completely missed. It turns out I was accidentally triggering these when buying back stocks too quickly after selling them at a loss. This was adjusting my cost basis in ways I didn't understand. It also created a really clear breakdown of short-term vs long-term gains that made it obvious why my tax bill was so high (almost everything was short-term). Definitely using this for next year's taxes too!

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Late to this thread but wanted to add something important - if your wife is doing enough trading to be considered a "trader" by IRS standards (which is pretty frequent activity), you might want to look into making a Section 475(f) election which lets you mark-to-market your securities. I went through this last year and spent WEEKS trying to get someone at the IRS to answer my questions. Kept calling the main line and getting disconnected after hours on hold. Finally discovered https://claimyr.com which got me through to an actual IRS agent in about 20 minutes. You can see how it works here: https://youtu.be/_kiP6q8DX5c The agent confirmed that as a day trader I needed to file some additional forms and gave me specific guidance that saved me thousands. Definitely worth it if you're doing more than occasional trading.

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How exactly does this service work? Do they just call the IRS for you or what? Seems weird that they could get through when nobody else can.

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Sounds like a scam. Nobody can get through the IRS phone tree. If this actually worked, everyone would be using it. Plus why would you need to talk to an IRS agent about day trading? Just read the publications.

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The service basically calls the IRS and navigates the phone system for you. They stay on hold so you don't have to, then when they reach an agent, they call you and connect you directly. You're the one who actually speaks with the IRS. Regarding why I needed to speak with an agent - the Section 475(f) election has very specific requirements and deadlines. The IRS publications give general information, but I had questions about my specific situation that weren't covered clearly. The agent was able to confirm exactly which forms I needed and the correct timing, which the general publications didn't make clear for my situation.

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I was completely wrong about Claimyr. After posting my skeptical comment, I decided to try it myself since I've been trying to get clarification on some trader tax status questions for MONTHS. I was shocked when they actually got me through to an IRS tax specialist within about 30 minutes. I had been trying on my own for weeks with no success - just endless holds and disconnections. The agent I spoke with clarified exactly how the trader tax status works with my specific situation (trading in both personal and retirement accounts). She explained that my retirement account trading doesn't count toward establishing trader status, which none of the tax articles I read had mentioned. Seriously saved me from making a mistake that could have triggered an audit. Sometimes you really do need to speak to someone official rather than just reading general guidelines.

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One thing nobody's mentioned yet - if your wife is doing this regularly, you might want to make quarterly estimated tax payments this year to avoid underpayment penalties. Day trading can create large tax bills that catch people by surprise. Also, keep perfect records of every single transaction. The IRS matches your 1099-B forms from brokerages against what you report, and any discrepancies will trigger notices. Some brokerages don't track wash sales across multiple accounts, so your tax software needs to do this.

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Thanks for mentioning the quarterly payments - that's something I hadn't considered at all. Do you know what the threshold is for when we need to start making those payments?

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Generally, you should make estimated tax payments if you expect to owe at least $1,000 in taxes when you file your return AND your withholding and credits will cover less than 90% of your current year tax or 100% of your previous year's tax (110% if your AGI was over $150,000). For active traders, it's almost always smart to make quarterly payments because the gains can be unpredictable and substantial. You can use Form 1040-ES to calculate and make these payments. The due dates are April 15, June 15, September 15, and January 15 of the following year.

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Has anyone run into issues with the wash sale rule while day trading? I'm wondering if the OP's wife needs to worry about this if she's buying and selling the same stock repeatedly.

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Oh yeah, wash sales can be a HUGE issue for day traders. If you sell a stock at a loss and then buy it again within 30 days before or after the sale, you can't claim that loss immediately. Instead, the loss gets added to the cost basis of the new purchase. For casual investors, this isn't a big deal, but for day traders who might be trading the same stocks repeatedly, it can create a massive tax tracking headache. Most tax software struggles with tracking this properly across multiple brokerages.

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