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Has anyone used TurboTax to handle this specific situation? I'm in the same boat with a PayPal 1099-K for gambling but not sure if the software can handle it correctly.
Thanks, that's really helpful! I was worried I'd need to hire an accountant instead. Do you remember if TurboTax has a specific section for the gambling log or if I need to create that separately?
TurboTax doesn't automatically generate a gambling log for you - you'll need to create that documentation separately. The software will ask you to enter your total gambling winnings and losses, but you're responsible for maintaining the detailed records (dates, locations, amounts, etc.) that the IRS requires. I'd recommend creating a simple spreadsheet with columns for date, gambling site/location, amount deposited, amount withdrawn, and net win/loss for each session. Keep this along with your PayPal transaction history and any screenshots from gambling sites. TurboTax will handle the tax calculations once you input the totals, but having that detailed backup documentation is crucial in case of an audit.
This is a really complex situation that I see come up a lot in tax forums. One thing I'd add to the excellent advice already given - make sure you understand the timing of when PayPal reports these transactions versus when your actual gambling activity occurred. Sometimes PayPal will issue a 1099-K based on when payments were processed through their system, which might not align perfectly with your actual gambling sessions. For example, if you deposited money in December 2022 but it didn't clear until January 2023, there could be timing differences that affect which tax year the activity should be reported in. Also, keep in mind that if you do end up owing taxes on this, the IRS offers payment plans that can help spread out the burden. But definitely get this sorted out correctly from the start - gambling income reporting errors can trigger audits, and you want to make sure your documentation is bulletproof. The separate account strategy mentioned by others is spot-on for future years. It's much easier to handle this when gambling transactions are completely isolated from your regular financial activity.
That's a really good point about the timing differences between when transactions are processed versus when gambling activity actually occurred. I hadn't thought about how year-end deposits could create complications across tax years. For anyone dealing with this situation, would you recommend adjusting the gambling log to match PayPal's processing dates rather than the actual gambling session dates? Or should we stick to reporting based on when the gambling actually happened and then reconcile any timing differences separately with supporting documentation? Also, regarding the payment plan option - is there a minimum threshold before the IRS will approve a payment plan for taxes owed on gambling income?
This thread has been incredibly helpful! I'm dealing with a PFL situation myself and had no idea about some of these nuances. One question I haven't seen addressed - what happens if you received PFL benefits in December but didn't actually take the leave until January of the following tax year? My daughter was born in late December, but I didn't start my actual leave until after the New Year due to how my company handles their leave policies. I received a lump sum payment in December for the upcoming leave period. Should this be reported on my 2024 return even though the leave itself was in 2025? I'm worried about getting this timing wrong since it seems like there are so many ways to mess up PFL reporting. Also, has anyone dealt with PFL from multiple states? We moved mid-year and I'm not sure if I need to file anything special since I was paying into one state's program for part of the year but used a different state's program for the actual leave.
Great questions! For the timing issue - PFL benefits are typically reported based on when you received the payment, not when you actually took the leave. So if you received that lump sum in December 2024, it should be reported on your 2024 tax return even though your leave was in 2025. The IRS generally follows the "constructive receipt" rule for income timing. For the multi-state situation, this gets more complex. You'll likely need to file returns in both states since you were paying into one state's system but used another's benefits. The state where you received the benefits will issue your 1099-G, and you may need to claim a credit on your original state's return for taxes paid to avoid double taxation. I'd definitely recommend consulting with a tax professional for this scenario since state tax treaties vary widely. You might also want to check if there are any proration rules that apply when you move between states mid-year - some states have specific provisions for this situation that could affect your tax liability.
I went through this exact same confusion with TurboTax and PFL benefits! You're right to be careful about getting it correct - the reporting requirements can be tricky. First, check your mail and online portals for a 1099-G form from your state's family leave program. This form should show the total PFL benefits you received and any taxes that were withheld. The 1099-G is separate from your W-2 because the payments come from the state fund, not directly from your employer. When you enter the 1099-G information in TurboTax, make sure you're putting it in the "Government Payments" or "1099-G" section, not trying to add it to your W-2 wages. TurboTax will walk you through this when you get to that section. One important thing to double-check: if your employer provided any "top-up" payments to supplement the state benefits (bringing you closer to your full salary), those employer contributions WOULD appear on your W-2. But the base PFL payments from the state should only be on the 1099-G. If you haven't received your 1099-G yet, contact your state's PFL department - they usually have online portals where you can access or request these documents. Don't file without it, as you'll likely need to amend your return later if you miss reporting this income.
This is super helpful, thank you! I'm actually in a similar boat as the original poster - took PFL after my son was born last fall and I'm completely lost on the tax implications. I haven't received a 1099-G yet either, so I'll definitely check my state's portal like you suggested. One thing I'm wondering about - do you know if the timing of when I applied for benefits versus when I actually received payments matters? I applied in August but didn't start getting payments until September. Just want to make sure I'm not missing anything when I finally get that 1099-G form.
Hey fellow tax warriors! š¤¦āāļø I've been trying to get through to the IRS for days about a notice I received for my small business. According to the IRS website (https://www.irs.gov/help/contact-my-local-office-in-person), they have different numbers for different issues, but I keep getting stuck in phone tree hell no matter which one I try. Has anyone figured out the magic sequence of buttons to press to actually speak with a human? I've tried calling early morning and right before closing time but no luck. I need to sort this out before my quarterly filing is due. Any tips from people who've successfully navigated this maze?
This is such a timely thread! I just went through this nightmare myself last month. After reading all these suggestions, I want to add that the IRS also has a specific line for amended returns at 866-464-2050 if that's what your notice is about. One thing I learned the hard way - when you finally do get through to someone, ask them to notate your account with what you discussed. I had to call back two weeks later about the same issue and the second agent had no record of my previous call. Now I always ask for a confirmation number or case number. Also, @Giovanni Mancini since you mentioned this is for your small business, definitely try that 800-829-4933 business line that @Ava Garcia mentioned. Even if the wait is still long, at least you'll be talking to someone who understands business tax issues rather than getting transferred around between departments. Good luck with your quarterly filing deadline!
This is incredibly helpful advice, @Xan Dae! I hadn't thought about asking for a confirmation number - that's such a smart tip. I've had similar experiences with other government agencies where they have no record of previous calls. Definitely going to try the business line first since this is related to my LLC. Really appreciate everyone sharing their experiences here - it's like having a support group for IRS phone system survivors! š
I feel your pain! Just went through this exact same struggle two weeks ago with a CP3219A notice for my consulting business. After reading through everyone's suggestions here, I tried a combination approach: 1. Called the business line (800-829-4933) that several people mentioned 2. Used the 7:30am Tuesday timing strategy 3. Had all my documents ready (EIN, notice number, previous year's return) Got through in about 40 minutes! The agent was actually knowledgeable about business tax issues and didn't transfer me around. She explained that my notice was just a computer-generated mismatch and walked me through the response process. One additional tip: when you do get through, ask them to send you a written summary of your call via mail. The agent told me this creates a paper trail that helps if you need to call back later. Also, if your notice has a specific response deadline, make sure to ask about penalty relief options if you're close to the due date. The whole experience reminded me why I'm considering hiring a tax professional next year - sometimes the peace of mind is worth the cost when dealing with business taxes!
Don't overlook the importance of matching what's on your 1099-B forms when amending. Your broker should have sent these forms showing your trading activity. Make sure what you're reporting matches these exactly. I went through a similar amendment and made the mistake of not having my forms in front of me when I redid everything. The IRS flagged it because the numbers didn't match what my broker reported. Caused a huge delay and I ended up having to redo the amendment.
Absolutely right. And don't forget to check if your broker already adjusted for wash sales on the 1099-B. I double-counted some wash sale adjustments when fixing my carryover issues and it created a complete mess that took two more amendments to sort out.
I'm dealing with a very similar situation right now - had significant losses in 2021 and 2022 that I didn't properly carry forward, and now I'm trying to clean everything up before filing my 2023 return. One thing I learned from my tax preparer is to be extra careful about the timing of when you file the amended return versus your current year return. While you don't have to wait for the amendment to be processed, you do want to make sure you're consistent in how you calculate your carryover losses between the two returns. Also, if you're using tax software for your 2023 return, most programs will ask you to manually enter your capital loss carryover from the previous year. Make sure you use the CORRECTED amount (including that missing $16k from 2021) rather than what actually appeared on your filed 2022 return. Keep detailed notes about this adjustment in case you need to explain it later. The good news is that in your case, the math works out nicely - your $10k gain in 2023 can be completely offset by your carryover losses, plus you'll still have losses remaining to carry forward to future years. Just make sure you document everything clearly!
Theodore Nelson
Thanks everyone for the detailed responses! This is super helpful. I had no idea about the FBAR requirement - definitely would have missed that completely. Just to clarify my situation: I earned this money while working in Germany on a work visa, and it's been sitting in my German bank account for about 2 years. I only got my green card and moved to the US 3 months ago. From what I'm understanding, I don't owe US taxes on the $21k itself since I earned it before becoming a US resident, but I do need to file the FBAR because my German account had more than $10k at some point this year. Do I also need Form 8938, or is that only if the account balance was even higher? The IRS thresholds are confusing me a bit. Also really appreciate the tips about keeping documentation - I definitely have my employment contract and bank statements from Germany that show the money came from my salary there.
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CaptainAwesome
ā¢For Form 8938, the thresholds depend on your filing status and where you live. Since you're unmarried and living in the US, you need to file Form 8938 if your foreign financial assets were worth more than $50,000 on the last day of the tax year OR more than $75,000 at any point during the year. So with $21k, you likely won't need Form 8938, just the FBAR. The FBAR threshold is much lower ($10,000) and applies to the maximum balance in all your foreign accounts combined at any point during the calendar year. Since you had over $10k in your German account this year, you'll definitely need to file that by April 15 (or October 15 with automatic extension). Smart thinking keeping those German employment records - that documentation will be valuable if anyone ever questions the source of the funds!
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Natasha Petrov
Welcome to the US tax system! Your situation is actually pretty common for new green card holders. Just wanted to add a couple of practical tips from my own experience with international transfers: 1. When you do transfer the money, consider doing it in smaller chunks (like $7k-8k at a time) rather than all $21k at once. This won't change your tax obligations, but it can sometimes get you better exchange rates and lower transfer fees depending on your banks. 2. Make sure to get a detailed transfer receipt showing the exchange rate used and any fees charged. These can be useful for your records, especially if you need to document the transaction later. 3. If your German bank charges high fees for international transfers, definitely look into services like Wise or Remitly - they often save hundreds of dollars on large transfers like yours. The good news is that Germany has a tax treaty with the US, so if you did have any taxable income from interest on that account while you were a US resident, you could potentially claim foreign tax credits to avoid double taxation. But for the principal amount you earned while working there, you're all set - no US taxes owed on the transfer itself!
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Luca Esposito
ā¢Great advice about breaking up the transfer! I did something similar when I moved my savings from Australia - ended up saving almost $300 in fees by using Wise instead of my bank's wire transfer service. One thing to add though: make sure you keep track of all the individual transfer amounts and dates for your records. Even though it doesn't create additional tax obligations, having a clear paper trail is always helpful if questions come up later during audits or immigration processes. Also, since you mentioned the Germany-US tax treaty, that's definitely worth understanding even though your principal won't be taxed. If your German account earned any interest while you were already a US resident (even just for those 3 months), you'd need to report that interest income on your US tax return. But you can often claim a foreign tax credit for any German taxes withheld on that interest, so you shouldn't end up paying twice on the same income.
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