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Don't forget you can also deduct your losses up to the amount of your winnings if you itemize deductions instead of taking the standard deduction. So if you won $195 but lost $100 getting there, you'd only owe taxes on $95 of gambling income. Just make sure you have records of both the wins AND losses!
Thais Soares
ā¢But isn't itemizing only worth it if all your deductions add up to more than the standard deduction? That's like $13,000+ for a single person. Seems like you'd need a lot more than some gambling losses to make itemizing worthwhile.
That's absolutely right. Itemizing only makes sense if your total deductions (including gambling losses, mortgage interest, certain state taxes, charitable contributions, etc.) exceed the standard deduction amount. For 2025, the standard deduction is projected to be around $13,850 for single filers. So unless you have significant other deductions, tracking gambling losses probably won't provide a tax benefit if your gambling activity is minimal like the OP's situation.
Nalani Liu
For small amounts like $195, most casual bettors just don't report it. Is it technically required? Yes. Will anything happen if you don't? Almost certainly not. The betting site won't report it to the IRS without hitting those W-2G thresholds others mentioned.
Axel Bourke
ā¢I wouldn't recommend this approach. Even small unreported income can cause issues if you're ever audited for other reasons. Better to report everything and stay clean.
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Jamal Brown
Something nobody has mentioned yet - depending on your situation, you might want to consider recharacterizing your Roth IRA contribution to a Traditional IRA instead of just withdrawing the excess. Since you're filing jointly with your spouse, your combined income might allow you to deduct a Traditional IRA contribution, which could be beneficial. This way you don't lose the tax-advantaged space completely. Talk to your IRA provider about the "recharacterization" process. It's different from a withdrawal and has different tax implications. You'd still need to do this before the tax filing deadline (plus extensions).
That's an interesting option I hadn't considered. If I recharacterize to Traditional IRA, would I still need to worry about the earned income limit? And would I need to do anything special on my tax forms?
Jamal Brown
ā¢You still need earned income to contribute to a Traditional IRA, but the same limit applies - your contribution can't exceed your earned income for the year. So you'd still need to recharacterize the excess amount above your $4,200 income. For tax forms, you would report the recharacterization on your tax return using Form 8606 if any portion is non-deductible. Your IRA custodian will also send you a statement showing the recharacterized amount, which you should keep with your tax records. The good thing is recharacterization isn't a taxable event if done properly and before the deadline, so you avoid the penalties associated with excess contributions.
Just wanted to point out that if you already filed your 2023 taxes, you may need to file an amended return depending on how you handle the excess contribution. Some people just pay the 6% penalty and deal with it, but that's usually not the best approach since the penalty applies every year until you fix the issue.
Actually, if you withdraw the excess contribution plus earnings before you file your taxes (and before the due date), you don't need to file an amended return. You just report the earnings portion on your current year taxes. The IRA custodian will issue a 1099-R for the withdrawal.
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One thing nobody mentioned yet - make sure you're keeping good records of all your investment purchases and sales! The IRS requires you to track your "cost basis" (what you paid for the investment) to calculate your gains or losses accurately. Most brokerages now report this information to the IRS on Form 1099-B, but sometimes the information is incomplete or incorrect. I learned this the hard way when I couldn't prove my original purchase price for some stocks I'd held for years.
Do you have any tips for how to keep track of all this? I've been investing through multiple platforms (Robinhood, Vanguard, and a little crypto on Coinbase) and I'm worried about keeping everything straight for next year's taxes.
I recommend downloading annual tax documents from each platform and saving them in a dedicated tax folder on your computer. Name each file with the year and platform (like "2025_Robinhood_1099.pdf"). For crypto especially, consider using a dedicated tracking app that can integrate with multiple exchanges to create a comprehensive tax report. Some platforms like CoinTracker or Koinly can sync with Coinbase and other exchanges to track your cost basis automatically. The few minutes spent organizing throughout the year will save you hours of stress during tax season.
Justin Trejo
Quick tip: If you're married filing jointly, the capital loss deduction limit is still $3,000 total (not $3,000 per person). My spouse and I found this out when we tried to deduct $6,000 in losses and got our return rejected.
Alana Willis
ā¢Are you sure about that? My accountant let us deduct $3,000 each last year. Maybe the rules changed for the 2025 filing season?
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Just wanted to add something important - if you're owed a refund for 2023, there's actually no penalty for filing late! The IRS doesn't penalize you for filing late if they owe YOU money. You have 3 years from the original due date to claim a refund. But if you do owe taxes like you mentioned, then yes, there are penalties and interest. Still, it's WAY better to file late than never. The IRS is generally pretty reasonable with people who come forward voluntarily vs. those they have to chase down.
Thanks for mentioning this! Unfortunately I'm pretty certain I owe them money since I had some 1099 income without any withholding. But that's good info to know for the future. Do you know if most tax preparers handle late returns like this or should I look for someone who specializes in them?
Most regular tax preparers can definitely handle late returns - it's pretty common and not as complicated as you might think. You don't need a specialized tax attorney or anything unless you have a really complex situation or owe an enormous amount. Any decent tax preparer or even the major tax software packages can guide you through filing a late return. They'll help calculate the penalties and interest too. If your situation is relatively straightforward (W2 income, maybe some 1099 work), you could even do it yourself with good tax software.
Don't panic! I went through this exact thing for my 2020 taxes. Depression is real and the IRS actually does understand that life happens. Quick tip - if you're worried about penalties, look into what's called "first-time penalty abatement" if you have a clean compliance history (meaning you filed and paid on time for the past 3 years before 2023). The IRS often waives penalties for your first offense if you call and explain your situation.
This is great advice! I got first-time abatement when I missed filing during my mom's cancer treatment. Saved me over $1,100 in penalties. The IRS agent was surprisingly understanding when I explained what happened.
Sean Kelly
One thing nobody's mentioned yet - if your income fluctuates a lot throughout the year (which is common for freelancers), you might want to look into the "annualized income installment method" instead of just dividing your expected tax by four. Basically, you can pay estimated taxes based on what you've actually earned so far each quarter, rather than paying equal amounts. It's a bit more complicated to calculate, but it's helpful if your income isn't consistent and you don't want to overpay early in the year. Form 2210 Schedule AI is what you'd use when filing. It's a bit more work but can really help with cash flow if your income is seasonal or unpredictable.
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Isabella Costa
ā¢This is super helpful - my income definitely fluctuates! How complicated is the calculation? Is there a simple formula I could use or do I need special software? I'm trying to avoid paying for a tax professional if possible.
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Sean Kelly
ā¢The calculation isn't super simple, but it's doable without professional help. You basically track your income, deductions, and credits for each payment period, then calculate the tax on that amount as if it were your annual income (annualizing it). There's no single formula since it depends on your particular tax situation, but the IRS has worksheets in Publication 505 that walk you through it step by step. Most tax software can help with this too if you input your quarterly income data. I'd recommend at least trying the calculation once to see if it's manageable for you. The benefit is that if you earn most of your income later in the year, you won't have to make large estimated payments before you've actually earned the money.
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Zara Mirza
Don't overlook state estimated taxes too! Everyone's talking about federal, but depending on your state, you might need to make state quarterly payments as well. Some states have different thresholds and due dates. For example, I'm in California and got hit with a penalty because I made federal quarterly payments but completely forgot about state ones my first year freelancing.
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Luca Russo
ā¢Good point! I'm in Texas so I lucked out with no state income tax, but my friend in New York had the same issue as you. Do most states use the same payment deadlines as the federal ones?
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