Do day traders and investors need to pay quarterly estimated taxes?
I'm fairly new to investing and just learned about quarterly estimated taxes. Is there a specific income threshold that requires me to start making these payments, or is this something all investors have to do regardless of how much they make? This is my first year trading stocks and ETFs. So far I've only made about $325 in realized capital gains and received around $35 in dividends. Am I flying under the radar here or am I going to get hit with penalties for not making these quarterly payments? Really don't want to mess this up on my first tax filing as an investor.
24 comments


Ella Harper
Yes, traders and investors may need to pay quarterly estimated taxes, but it depends on your overall tax situation. The IRS generally expects you to pay taxes as you earn income throughout the year, not just at tax filing time. There are some thresholds that might help you. Generally, you need to make estimated tax payments if you expect to owe at least $1,000 in taxes when you file your return AND your withholding and refundable credits will cover less than 90% of your current year's tax or 100% of last year's tax (110% if your AGI was over $150,000). With only $325 in capital gains and $35 in dividends, you're likely fine without making quarterly payments, especially if you have a regular job with tax withholding that covers your overall tax liability. These investment earnings are relatively small and probably won't trigger enough additional tax to require quarterly payments.
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PrinceJoe
•What if I'm self-employed and also investing? Does that change things? My trading isn't huge but I have a small business too.
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Ella Harper
•If you're self-employed, that definitely changes the situation. Self-employment income is not subject to automatic withholding like a W-2 job, so you're generally expected to make quarterly estimated tax payments on that income. The investment income would be combined with your self-employment income when determining if you meet the threshold for quarterly payments. Since self-employment taxes include both the employee and employer portions of Social Security and Medicare (15.3% total), even modest self-employment earnings can quickly create a tax liability exceeding $1,000, triggering the quarterly payment requirement.
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Brooklyn Knight
After getting audited last year for missing some investment income reporting, I started using https://taxr.ai to make sure all my trading activity is properly reported. The software scans all my trading statements and tax documents, then tells me exactly what I need to report on Schedule D and whether I've hit the threshold for quarterly payments. I used to be so confused about which trades would trigger quarterly payment requirements, especially with options trading where determining the correct cost basis was a nightmare. The tool saved me hours of work and showed me I was actually under the threshold where quarterly payments were required.
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Owen Devar
•Does it work if you have crypto trading too? My brokerage is pretty straightforward but I have like 5 different crypto platforms and I have no idea how to track all that for taxes.
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Daniel Rivera
•I'm skeptical about these tax tools. Does it actually connect to your brokerage accounts directly or do you have to upload statements? I've tried other tax programs and they always mess up the wash sale calculations when I have trades across multiple accounts.
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Brooklyn Knight
•Yes, it absolutely works with crypto trading! That's actually one of the main reasons I started using it. It can process transactions from all the major crypto exchanges and even many of the smaller ones. You just connect your accounts or upload the transaction history, and it figures out your cost basis and capital gains across all platforms. For traditional brokerage accounts, you can either connect them directly or upload your statements - I prefer uploading my year-end tax documents because it's simpler. And regarding wash sales, it properly handles them across multiple accounts as long as you provide all your trading data. It flagged several wash sales I had between my main account and my IRA that I would have completely missed otherwise.
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Daniel Rivera
I was initially skeptical about taxr.ai since I've been burned by tax software before, but I gave it a try after struggling with my crypto taxes. I was shocked at how well it worked. I had trading on Coinbase, Binance, and a couple smaller exchanges, plus some staking rewards I'd completely forgotten about. The tool identified exactly which trades pushed me over the threshold for quarterly tax payments and gave me clear guidance on when and how much to pay. Turns out I was way over the limit and would have faced penalties without knowing it. They even have a calendar feature that sends reminders before each quarterly payment is due. Definitely worth checking out if you're doing any significant trading.
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Sophie Footman
For anyone struggling to get through to the IRS about investment tax questions, I finally had success using https://claimyr.com to get through to an actual IRS agent. I had been trying for WEEKS to get clarification on my quarterly payment requirements after selling some inherited stocks. Their system held my place in line with the IRS and called me back when an agent was available. You can see how it works here: https://youtu.be/_kiP6q8DX5c. The IRS agent I spoke with walked me through exactly how to calculate my required quarterly payments based on my projected trading income, and explained which form to use. Saved me hours of frustration and hold music!
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Connor Rupert
•How does this actually work though? The IRS phone system is notoriously impossible. Does Claimyr just keep auto-dialing until they get through?
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Molly Hansen
•Sounds like a scam honestly. Why would I pay someone else to call the IRS for me? Plus how do they get priority access when regular people can't get through? I bet they're just selling your info to marketers.
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Sophie Footman
•They use a system that navigates the IRS phone tree and holds your place in the queue. It's not auto-dialing - they actually maintain the connection with the IRS while you go about your day, then they call you when they've reached an agent and bridge the call. So you're speaking directly with the IRS, not with Claimyr. No, they don't sell your information. They make money from the service fee, not from data. And they don't have "priority access" - they just save you from having to personally wait on hold for hours. Think of it like hiring someone to stand in line for you at the DMV. When they get to the front, they call you over for your actual appointment.
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Molly Hansen
I have to admit I was completely wrong about Claimyr. After that snarky comment I made, my curiosity got the better of me and I tried it when I needed to sort out a form 1099-B discrepancy with the IRS. Waited THREE DAYS trying to call myself with no luck. Used their service and got a callback with an actual IRS agent within 2 hours. The agent was able to explain exactly how my stock sales needed to be reported and confirmed I was under the threshold for mandatory quarterly payments. Saved me from overpaying by about $450. Sometimes being wrong feels pretty good!
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Brady Clean
For new investors, the safe harbor rule is your best friend. If your W-2 withholding covers at least 100% of your previous year's tax liability (or 110% if you make over $150k), you won't face underpayment penalties even if you have investment gains. That's why I just increase my W-2 withholding slightly rather than dealing with calculating and making separate quarterly payments. Way simpler than trying to project my trading profits four times a year!
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Micah Franklin
•Does that safe harbor approach work even if you have significantly more investment income this year compared to last year? My portfolio's doing much better this year than last.
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Brady Clean
•Yes, that's exactly the beauty of the safe harbor rule! Even if your investment income jumps dramatically this year, as long as your withholding covers 100% of last year's total tax (or 110% for higher incomes), you're protected from underpayment penalties. This works because the safe harbor is based on your previous year's tax liability, not your current year's income. So if you had a total tax liability of $10,000 last year, and ensure your withholding this year will be at least $10,000, you won't face penalties even if your actual tax bill ends up being $15,000 due to investment gains. You'll still owe the additional $5,000 when you file, but without the underpayment penalties.
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Skylar Neal
Watch out for state quarterly requirements too! Federal is just one piece. I made the mistake of thinking I was fine because my federal withholding met the safe harbor, but my state (CA) has different rules and I got hit with a $190 penalty last year on just $4k of trading profits.
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Vincent Bimbach
•Not all states have the same rules though. Here in Texas we have no state income tax so all I worry about is federal. But good reminder for people in states with income tax!
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Yuki Tanaka
Great question! Based on your numbers ($325 in capital gains and $35 in dividends), you're almost certainly fine without quarterly payments. That's only $360 in investment income, which even at the highest tax rates wouldn't generate enough tax liability to trigger the $1,000 threshold. The key thing to remember is that quarterly estimated taxes are based on your TOTAL tax situation, not just investment income. If you have a regular W-2 job with withholding, that withholding likely covers your entire tax liability including these small investment gains. One tip for next year: keep track of your realized gains throughout the year. If you start seeing bigger profits (say, over $3,000-4,000 in gains), that's when you might want to calculate whether you need to start making quarterly payments or increase your W-2 withholding. But for your first year with these amounts, you should be totally fine!
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Joy Olmedo
Just wanted to add some perspective as someone who's been through this exact situation. When I first started trading, I was terrified about quarterly taxes too, but with your income levels you're definitely in the clear. The $1,000 threshold that others mentioned is key - even if you paid the highest marginal tax rate on your $360 in gains, you'd only owe about $80-90 in additional taxes. That's nowhere near the $1,000 minimum that triggers quarterly payment requirements. One thing that really helped me was setting up a simple spreadsheet to track my realized gains throughout the year. That way I could see when I was approaching levels where I might need to worry about quarterly payments. For your first year, just focus on learning the basics of tax reporting for investments. You can always reassess next year if your trading activity increases significantly. Also, don't forget that you can deduct up to $3,000 in capital losses against ordinary income if you have any losing trades. Sometimes new investors focus so much on the gains that they forget losses can actually help reduce their tax bill!
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Felicity Bud
•This is really helpful advice! I'm in a similar boat as the original poster - just started investing this year and have been worried about whether I'm doing everything right tax-wise. The spreadsheet idea is brilliant, I'm definitely going to set that up to track my gains and losses throughout the year. One quick question - when you mention deducting up to $3,000 in capital losses, does that apply even if I'm mostly trading ETFs and index funds rather than individual stocks? I've had a few small losses on some positions but wasn't sure if the same rules applied to all types of investments.
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Daniel Price
•@fc89033d6fb5 Yes, absolutely! The capital loss deduction rules apply to all types of investments - stocks, ETFs, index funds, bonds, crypto, you name it. It doesn't matter what type of security you're trading, as long as it's a capital asset. The $3,000 annual limit applies to your net capital losses (total losses minus total gains). So if you have $1,000 in gains and $2,000 in losses, you can deduct $1,000 against ordinary income. If you have larger net losses, you can carry the excess forward to future years. ETFs and index funds are actually pretty tax-efficient compared to individual stocks, but you can still have losses from selling positions at a loss or from volatility. Just make sure to watch out for wash sale rules if you're buying and selling the same or "substantially identical" funds within 30 days - that can disallow the loss deduction.
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Kayla Jacobson
As someone who started trading last year, I can relate to your concerns! With only $325 in capital gains and $35 in dividends, you're definitely not going to trigger any quarterly payment requirements. Those amounts are so small that even at the highest tax rates, you'd owe maybe $70-80 in additional taxes - nowhere near the $1,000 threshold that would require quarterly payments. The bigger picture here is that quarterly estimated taxes are really designed for people with significant income that isn't subject to withholding (like self-employment income or major investment gains). If you have a regular job with tax withholding, that withholding almost certainly covers your small investment gains. My advice: don't stress about it for this year, but do start keeping better records now. Create a simple log of your trades and gains/losses so you can monitor when you might cross into territory where quarterly payments become necessary. Most people don't need to worry about this until they're making several thousand in investment income annually. You're definitely flying under the radar in a good way!
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Steven Adams
•This is exactly the reassurance I needed to hear! I've been losing sleep over this thinking I was going to get hit with some massive penalty for not knowing about quarterly payments. It's such a relief to know that with my small amounts I'm well under any threshold that would matter. I really like your suggestion about keeping better records going forward. I've just been kind of winging it with a basic app to track my portfolio, but creating a proper log of trades and gains/losses sounds like a smart move as I get more serious about investing. Do you have any recommendations for simple ways to track this stuff, or is a basic spreadsheet the way to go for someone just starting out?
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