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Ask the community...

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Mei Lin

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Just wondering if anyone knows if the threshold for receiving a W-2G form for sports betting? I won a $2,100 parlay but never got any tax form from the betting site.

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For most gambling, the threshold is $600, BUT sports betting is different. For sports bets, you generally only get a W-2G if the winnings are at least $600 AND the odds were at least 300-to-1 (so basically huge parlay wins). Even without a W-2G though, you're still legally required to report ALL winnings.

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This is such a timely question! I went through the exact same confusion last year as a new bettor. The gross vs net reporting requirement is definitely counterintuitive, but unfortunately that's how the IRS treats gambling income. One thing that really helped me was setting up a simple tracking system from day one this year. I created a basic spreadsheet where I log each bet - date, platform, amount wagered, outcome, and running totals of wins/losses. It takes maybe 30 seconds per bet but saves hours during tax season. Also worth noting - if you're betting regularly, you might want to consider whether itemizing deductions makes sense for you next year. Even if the standard deduction is higher this year, your situation might change. I ended up itemizing for the first time because between my gambling losses, charitable donations, and some medical expenses, it actually saved me money. The key is just staying organized and keeping good records. The platforms are getting better at providing tax documents, but having your own backup records gives you peace of mind. Good luck with your taxes!

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Liam O'Reilly

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This is really helpful advice! I'm also new to sports betting and taxes, so I'm curious - when you say you ended up itemizing, did you actually save money even though your gambling losses might have been less than the standard deduction? I'm trying to figure out if it's worth keeping track of other potential deductions like charitable donations throughout the year, or if I should just expect to take the standard deduction and eat the tax on gross winnings.

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Jamal Carter

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Has anyone dealt with the reporting requirements for the PERSON WHO PAID the settlement? I'm on the other side of this - I had to pay a settlement last year and am confused about how to report the attorney fees portion on the 1099-MISC I'm issuing.

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Mateo Perez

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Yes, as the payer of a settlement, you should issue a 1099-MISC to the recipient with the full settlement amount. If you paid their attorney directly, you would issue a separate 1099-MISC to the law firm for the attorney fees portion. For the 1099-MISC to the attorney, you'd report the payment in Box 3 as "Other income." For the 1099-MISC to the recipient, you'd include the total settlement amount (including the attorney fees) in the appropriate box depending on the nature of the settlement.

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Javier Torres

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Just want to add some clarity based on my experience as a tax preparer - the key thing everyone's touching on is correct: if your settlement was SOLELY for physical injuries from your workplace accident, it's likely not taxable under IRC Section 104(a)(2). However, be careful about one thing: if any portion of that $42,500 was for lost wages or punitive damages (rather than just compensating for the physical injury and medical expenses), that portion WOULD be taxable. Check your settlement agreement carefully - sometimes these get lumped together. If it's truly all for physical injuries, you don't report it as income, and the 1099-MISC in Box 3 becomes irrelevant for your tax return. But keep all your settlement documentation because the IRS will have a record of that 1099-MISC being issued to you. Also, even if you determine it's non-taxable, some tax software will still prompt you to enter the 1099-MISC and then allow you to mark it as "not taxable due to physical injury settlement" or similar - this creates a paper trail showing you received and considered the form.

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Omar Hassan

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This is really helpful clarification! I'm dealing with a similar situation and wondering - how do you actually determine what portion of a settlement is for physical injuries versus lost wages? My settlement agreement has some pretty general language about "damages arising from the incident" but doesn't break it down specifically. Would the way the settlement is structured in the agreement affect the tax treatment, or is it more about the underlying facts of what happened?

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Kendrick Webb

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Just to clarify something I learned the hard way... the health insurance coverage question (shared responsibility payment) was effectively eliminated after 2018 due to the Tax Cuts and Jobs Act setting the penalty to $0. So technically you don't have to worry about reporting health insurance coverage on federal taxes anymore, unless you live in a state that has its own individual mandate (like MA, NJ, RI, CA or DC).

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Hattie Carson

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Thats not completely accurate. Even though the federal penalty is $0, some tax software still asks about health insurance coverage because certain states DO still have penalties. I got hit with a penalty in California because i didnt report my coverage correctly even though the federal penalty is gone!

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Landon Morgan

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Great question! As others have confirmed, since you're a dependent covered under your mom's marketplace plan, you don't need to include the 1095-A on your tax return. Your mom, as the policyholder, is responsible for reporting it on her taxes. Just a couple of things to keep in mind as you file: 1. Make sure you check the box indicating that someone else can claim you as a dependent 2. You'll still report that you had health insurance coverage for the months you were covered (even though there's no federal penalty anymore, it's good practice) 3. Keep a copy of that 1095-A for your records - you never know when you might need it later Since this is only your second time filing, don't stress too much! You're asking the right questions. The main thing is accurately reporting your income from your campus job and correctly indicating your dependent status. The 1095-A situation is entirely your mom's responsibility to handle.

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CyberSamurai

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This is really helpful advice! I'm actually in a very similar situation - just started college and my parents handle most of the tax stuff but I have my own part-time income now. It's reassuring to know that the 1095-A isn't something I need to worry about on my return. One quick follow-up question though - when you say to report having health insurance coverage, is that just answering yes/no on the tax form, or do I need to provide specific details about the coverage dates? I was covered the full year under my parents' plan but want to make sure I'm answering correctly.

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Ella Cofer

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Has anyone dealt with handling PMI deduction in this situation? My boyfriend and I bought last year too and we have mortgage insurance since we put less than 20% down.

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Kevin Bell

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Unfortunately, the PMI deduction expired for tax years after 2021. It hasn't been extended for 2023 taxes yet, so currently you can't deduct PMI at all regardless of whose name is on the forms. Things might change if Congress retroactively extends it, but as of now, don't count on that deduction.

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Ella Cofer

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Ugh that sucks - I thought we could still deduct that! Our lender made it sound like it was a tax advantage. Thanks for letting me know before I tried claiming it.

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StarStrider

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This is such a helpful thread! I'm in a similar situation - my partner and I bought a house last year but aren't married yet. One thing I wanted to add is about property tax payments. Even if your mortgage company handles the property tax payments through escrow, you can still deduct those taxes on your return. Make sure to check your annual escrow statement from your lender - it should show exactly how much was paid in property taxes for the year. This amount can be deducted separately from the mortgage interest, and the same rules apply about splitting it between you and your fiancΓ© if you're both contributing to the mortgage payments. Also, don't forget about any points you paid when you got the mortgage - those are typically deductible in the year you bought the house if it was your primary residence. The points would be shown on your HUD-1 settlement statement or Closing Disclosure from when you purchased. Good luck with your taxes and congratulations on the house! The first year of homeownership taxes can be confusing but you'll get the hang of it.

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Thank you for mentioning the points deduction! I completely forgot about that. We did pay points at closing to get a lower interest rate, and you're right - I can see them on our closing documents. One quick question about the property taxes through escrow - do I use the amount that was actually paid to the county during 2023, or the amount that was deposited into escrow during 2023? Our escrow analysis shows these are slightly different amounts because of how the timing worked out with our closing date. Also, does anyone know if the property tax deduction is subject to the $10,000 SALT cap when filing as single? I know married couples are limited to $10k total, but I'm not sure how it works for unmarried people who own property together.

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CyberNinja

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I went through this exact same situation with IBKR about 6 months ago and it was a real eye-opener! Here's what I learned that might help you: IBKR's routing is largely automatic based on regulatory requirements and market access rules. Unfortunately, you can't really force them to keep everything with the US entity - when you buy European securities directly, they often MUST go through IBKR UK or other local entities due to MiFID II regulations and other local market rules. The good news is that if you're proactive about tracking this, it's manageable. I created a simple spreadsheet where I track: - Which securities are held by which IBKR entity (from monthly statements) - The maximum monthly balance for each foreign entity - Running totals to monitor FBAR thresholds One key thing I discovered: even if your total IBKR account value is below $10K, you might still hit the FBAR threshold if the foreign-held portion alone exceeds $10K. The reporting is based on the foreign accounts specifically, not your total investment portfolio. My advice would be to start tracking now even if you're below the threshold. It's much easier to have clean records from the beginning than to reconstruct everything later when you're scrambling to file. Plus, international investing tends to grow quickly once you get started, so you might hit those thresholds sooner than expected. The IRS has been increasingly focused on these compliance areas, so better safe than sorry!

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This is incredibly helpful information, thank you! I'm definitely going to start tracking this right away. The point about the foreign-held portion potentially hitting $10K even when your total account is smaller is something I never would have considered. Quick follow-up question - when you're tracking the "maximum monthly balance for each foreign entity," are you looking at the market value of just the securities held by that entity, or does it include things like cash balances and accrued interest too? I want to make sure I'm capturing everything that would count toward the FBAR threshold. Also, do you happen to know if there are any specific timeframes I should be worried about? Like, if I briefly crossed the $10K threshold for just a few days in a month due to market fluctuations, does that still trigger the reporting requirement? The spreadsheet approach sounds like a great way to stay organized - I'm usually pretty good with record keeping but this foreign entity tracking is a whole new level of complexity I wasn't prepared for!

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MidnightRider

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I've been dealing with this same issue for the past year and wanted to share some practical insights that might help others navigate this complex situation. First, regarding IBKR's entity structure - it's important to understand that this isn't necessarily something they're trying to hide, but the routing happens automatically based on regulatory requirements. When you trade European securities, for example, post-Brexit regulations often require those trades to go through IBKR UK rather than the US entity. Here's what I've learned about the practical aspects: **For tracking purposes:** You need to monitor the aggregate value of ALL accounts with foreign financial institutions, not just individual securities. So if you have $8K in IBKR UK and $3K in another foreign account, you've crossed the $10K FBAR threshold. **Timing matters:** The FBAR threshold is based on the highest aggregate balance at ANY point during the calendar year. Even if you hit $10,001 for just one day due to market gains, you're required to file. This is why real-time tracking is so important. **Beyond just stocks:** Don't forget that foreign currency balances also count. If IBKR holds EUR or GBP cash balances in foreign entities (which they often do for settlement purposes), those contribute to your threshold calculations too. One thing that surprised me was that IBKR's year-end tax documents don't clearly break down foreign vs. domestic custody arrangements, so you really need to stay on top of the monthly statements throughout the year rather than trying to reconstruct everything at tax time. The learning curve is steep, but once you get systems in place for tracking, it becomes much more manageable. The key is starting that tracking before you think you need it!

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