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Help Needed: Gambling Losses & PayPal 1099-K Issues with IRS Reporting

Hey everyone, I'm at my wit's end dealing with an IRS nightmare that's been going on for 5 years now. Back in 2020, I went through a phase where I did way too much sports betting online (thankfully with some help I've gotten that under control). My issue is with PayPal and how they reported my gambling activities to the IRS. I used PayPal for depositing and withdrawing from various betting sites. In total, I deposited about $337k and withdrew around $285k, so I ended up with a net loss of roughly $52k. Here's where it gets crazy - PayPal never sent me a 1099-K, but apparently reported to the IRS that I had "earnings" of $170k. I didn't even know this was happening until the IRS rejected my return in 2022. What PayPal seems to be doing is counting some of my withdrawals from gambling sites as if people were paying me for goods and services like I'm running a business! The problems are: 1) The $170k PayPal reported doesn't match my $285k in withdrawals, so I have no idea what they're counting and what they aren't 2) This number should be ZERO since I'm not a business and never conducted any business through PayPal I've worked with a tax pro from Jackson Hewitt who has refiled multiple times. We've provided win/loss statements, full transaction logs, and even added the $170k as Gambling Income on Schedule C with corresponding losses, but the IRS keeps rejecting the return. Has anyone dealt with PayPal misreporting gambling transactions? Any advice would be so appreciated!

Has anyone tried getting PayPal to issue a corrected 1099-K? I'm having the exact same issue where they're counting my DraftKings withdrawals as business income.

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Dylan Evans

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Good luck with that. I tried for months to get PayPal to correct mine. Called multiple times, sent emails, even had my accountant contact them. They just kept telling me "we report based on our system categories" and wouldn't budge.

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Olivia Clark

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This is such a frustrating situation that unfortunately many people are dealing with. PayPal and other payment processors often categorize gambling transactions incorrectly because their systems aren't designed to distinguish between different types of money transfers. A few additional points that might help: 1) When working with your tax professional, make sure they're familiar with gambling tax issues specifically. Not all tax preparers understand the nuances of how payment processors report gambling transactions. 2) Consider requesting your complete PayPal transaction history going back to 2020 and cross-reference it with your gambling site records. Sometimes the discrepancy between what PayPal reported ($170k) and your actual withdrawals ($285k) is because they're only counting certain types of transactions or excluding some transfers. 3) If you haven't already, document EVERYTHING - screenshots of your betting account histories, bank statements showing transfers to/from PayPal, and any correspondence with PayPal about the issue. 4) You might also want to consider filing a complaint with the Consumer Financial Protection Bureau (CFPB) against PayPal for incorrect reporting. While it won't immediately fix your tax situation, it creates an official record of the issue. The fact that you have win/loss statements and transaction logs is great - that documentation will be crucial in proving your case to the IRS. Don't give up!

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Yara Sayegh

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This is really helpful advice! I'm dealing with a similar issue where Venmo is reporting my poker winnings incorrectly. The CFPB complaint idea is interesting - I hadn't thought about creating an official record of the payment processor's error. One question though - when you mention getting complete PayPal transaction history, is there a specific way to request this? I've been trying to get more detailed records from Venmo but they only seem to provide basic transaction summaries. Having the full history like you described would definitely help me cross-reference with my gambling site records. Also, @764e0abb033b do you know if there's a statute of limitations on how far back the IRS can go with these kinds of discrepancies? I'm worried they might start questioning my returns from previous years too.

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CP05 Notice + IRS Letter About Phantom Amended Return - $5,000 Frivolous Filing Penalty Waived for Return I Never Filed - No Refund Movement Since February

Just got a CP05 letter saying I need to wait 120 days for my refund while they verify my wages. Has anyone gotten this? My transcripts show no movement since February and I'm really getting worried about my refund. Starting to feel hopeless about this whole thing. Today I received another letter from the IRS dated May 03, 2024, in response to something I supposedly submitted on May 02, 2024. The letter states word for word: "Dear Taxpayer: Thank you for your response of May 02, 2024. We're sending your response, dated May 02, 2024, to the office at the address at the end of this letter because: Your amended return corrected your frivolous position; therefore, will not be assessed the $6,000.00 frivolous filing penalty. However, your amended return included other changes which require further examination. You will be contacted if additional information is needed to process your case. Find tax forms or publications by visiting IRS.gov/forms or calling 800-TAX-FORM (800-829-3676). If you have questions, you can call 866-883-0235. If you prefer, you can write to the address at the top of the first page of this letter. When you write, include a copy of this letter, and write your telephone number and the hours we can reach you. Keep a copy of this letter for your records. Thank you for your cooperation." I'm completely confused because I never filed an amended return or had any "frivolous position" that needed correcting. I just filed my regular taxes and was expecting my refund. Now I have both the CP05 saying to wait 120 days AND this new letter talking about amended returns and penalties that I don't understand. The letter mentions a $6,000.00 frivolous filing penalty that they're not assessing me, but I never filed anything frivolous! It also says my "amended return included other changes which require further examination" but I never submitted an amended return at all. Has anyone dealt with this combination of issues before? I'm completely lost and feeling even more hopeless about ever seeing my refund. My transcripts still show absolutely no movement since February. Should I call the number they provided (866-883-0235)? Or should I write to them as suggested in the letter? I'm worried if I contact them it might delay things further, but I also want to clear up whatever confusion is happening here.

Ravi Patel

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Pro tip: upload your stuff to taxr.ai - saved me so much stress with my CP05. It actually predicted when my refund would hit within 2 days! Better than playing guessing games tbh

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for real? might have to check this out

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That letter about the amended return and frivolous filing penalty is really concerning - especially since you never filed an amended return! This sounds like identity theft or the IRS mixed up your case with someone else's. I'd definitely call that number (866-883-0235) ASAP to get this sorted out. Don't worry about it delaying your refund - if someone filed fraudulent documents under your SSN, that needs to be addressed immediately. Document everything and ask for a case number when you call. The CP05 might actually be related to this mix-up rather than normal verification.

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Taylor Chen

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This is really good advice! @Amina Bah you should definitely call that number - the combination of CP05 + a letter about an amended return you never filed is a huge red flag. Could be identity theft or they mixed up your case with someone else. Better to get it sorted now than wait and have bigger problems later. When you call, ask them to verify what documents they have on file for your SSN and get everything in writing!

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Adrian Connor

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Tax professional here: This is standard procedure for Louisiana's verification program. They randomly select returns to verify income reporting accuracy. Best practices: 1) Send copies not originals 2) Use certified mail 3) Keep proof of mailing 4) Include letter reference number on all docs 5) Make copies of everything you send. Average processing time after docs received is 30-45 days. Pro tip: Use taxr.ai to analyze your federal transcripts first - it can help identify any discrepancies that might trigger state reviews. Worth the $1 cost to avoid headaches later.

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Aisha Jackson

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How much does the certified mail usually cost?

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Adrian Connor

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Around $4-5 with tracking. Worth every penny for peace of mind!

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Same thing happened to me last year! I was freaking out at first but it really is just routine. Louisiana does these verification checks pretty regularly. I sent in copies of everything they requested and got my refund about 5 weeks later. Just make sure you respond within their deadline - I think they give you like 30 days to send the docs. Don't stress too much about it!

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Sean Doyle

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Does anyone know how the IRS even finds these fake businesses? Like, what triggers them to look at someone's return?

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Zara Rashid

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The IRS has several automatic triggers in their system. Businesses that consistently show losses (especially if they offset W-2 income) get flagged. They also use statistical models to compare your business expenses to others in your industry - if you're way outside the norm, you get flagged. Another big one is lifestyle mismatch - if your reported income doesn't match your lifestyle (nice house, expensive cars, etc). They also get information from banks about large transactions, and they have a whistleblower program where people can report suspected tax fraud.

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Your neighbor is walking into a financial disaster. What he's describing isn't a "brilliant tax strategy" - it's textbook tax fraud that the IRS specifically targets. The IRS has sophisticated algorithms that flag exactly this type of behavior: new LLCs with no real revenue, excessive business deductions that offset W-2 income, and patterns that don't match legitimate business activity. They're especially good at catching "hobby businesses" or shell companies created solely for tax avoidance. The fact that he's openly bragging about it makes it even worse from a legal standpoint. If audited, the IRS will want to see: - Proof of business purpose for every expense - Documentation showing exclusive business use (for home office) - Evidence that meals were actual business meetings - Legitimate business activity generating income Without these, he's looking at owing all the back taxes plus penalties that can range from 20% to 75% of the unpaid amount. In severe cases of willful fraud, there can even be criminal charges. The IRS gives people enough rope to hang themselves with - they'll often let this behavior continue for a few years before striking. When they do audit, they typically go back 3-6 years and scrutinize everything. Your neighbor needs to stop this immediately and consult with a legitimate tax professional to clean up his situation before it gets worse.

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Naila Gordon

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Just want to add that if the father suddenly decides to file taxes after several years of not filing, he could face penalties and interest from the IRS for those missed years. If he pushes this issue, it might end up costing him more than whatever he'd get from half the child tax credit.

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Cynthia Love

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This is an important point. The IRS can look back 6 years typically (sometimes more if they suspect serious issues). He might be opening himself up to scrutiny by suddenly filing again after a gap.

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The bottom line is that your girlfriend has no legal obligation to share the child tax credit with her ex, especially since he hasn't been filing taxes for years. The IRS rules are clear - whoever claims the child as a dependent on their tax return gets the credit. Since she's already filed and received her refund, and he hasn't filed taxes in 4-5 years, there's no mechanism for him to claim the child or the credit unless he suddenly decides to file this year. Even then, his return would likely be rejected since she already claimed the child. The 50/50 custody arrangement doesn't automatically entitle him to half the tax benefits. Tax law and custody arrangements are separate issues. Unless they have a written agreement or court order specifically addressing how tax benefits should be split, she's under no obligation to share. If he's serious about wanting tax benefits, he should start filing taxes consistently and they can work out an alternating years arrangement for future tax seasons. But for this year, the credit is rightfully hers since she's the one who actually filed and claimed the child.

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