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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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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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Freya Larsen

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There's another important factor to consider: SBTPG's batch processing schedule. They typically transmit funds to banks in specific windows (10am, 2pm, and 6pm Eastern Time are common processing times). If your trace number appeared after today's final batch, it will go in tomorrow's first batch. Also, be aware that SBTPG's system sometimes shows the trace number before they've fully processed your refund - the status should change to "Funded" when it's actually been sent to Chime. This can affect ACH transfer timing significantly.

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Hugo Kass

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I'm in a similar situation right now! Got my SBTPG trace number yesterday evening and have been refreshing my Chime account every hour since then. Based on what everyone's saying here, it sounds like I should see the deposit by tomorrow morning at the latest. This is my first time using TurboTax with the refund processing fee option, so I wasn't sure what to expect with the timing. Really helpful to see all these real experiences with the SBTPG → Chime timeline. Fingers crossed we both wake up to good news tomorrow!

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For those who have been through this before: Does having the trace number guarantee the money will arrive on the DDD? Here's what I understand so far: Step 1: IRS approves refund (shown on transcript) Step 2: IRS sends money to SBTPG (the "funded" status) Step 3: SBTPG issues trace number Step 4: Money arrives at Chime Is there anything else that could delay it at this point?

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Jamal Carter

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In my experience last year, once I had the trace number it was basically guaranteed. I remember being in the same position - checking SBTPG constantly and refreshing my bank app. The trace number appeared on Friday afternoon and I had my money Saturday morning with Chime. The only time I've seen delays after getting a trace number was when there was a banking holiday or when someone had an account issue (wrong account number, closed account, etc).

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Since your DDD is 02/26/2024, which is a Monday, have you noticed any pending deposits in your Chime account yet? I'm trying to understand if Chime actually shows pending deposits before they clear or if they just appear suddenly. My DDD is 03/04/2024 and I'm trying to plan accordingly.

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Thanks for sharing your timeline - this is really helpful for those of us waiting! I'm in a similar situation with a cycle 05 transcript that updated Friday, but I haven't gotten my trace number yet. SBTPG shows "funded" as of yesterday evening. Quick question: did you have to keep refreshing the SBTPG portal to see the trace number, or did they send you any kind of notification? I'm trying to figure out if I should be checking constantly or if there's a better way to monitor the progress. Also hoping my funds come through soon since I have some urgent expenses coming up too.

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