Will I get a 1099K from Venmo for sports betting withdrawals?

So if Venmo/PayPal doesn't send a 1099-K because I'm under the threshold, does that mean the IRS won't know about the money? And if BetMGM doesn't send any tax forms either, how would the IRS even find out? Just wondering...

The IRS can still find out about unreported income through various means, including bank deposits, audits, and information from third parties. The legal obligation to report all income exists regardless of whether you receive a tax form. Gambling establishments like BetMGM are required to issue W-2G forms for certain gambling winnings above specific thresholds (generally $600+ for most gambling, with higher thresholds for certain games). So you might still receive documentation from them directly.

Does it actually work with payment platforms like Venmo specifically? I've got a similar situation except mine's with FanDuel withdrawals going to Venmo, and I'm not sure if I should be tracking these differently than direct deposits.

Couldn't you just use TurboTax or something? Why pay for another service when the big tax software companies probably cover this stuff already?

Yes, it works with Venmo, PayPal, Cash App and all the major payment platforms. It specifically helps categorize those transactions correctly so you don't double-count income or miss deductions. It can even identify which transfers are just moving money between accounts versus actual income. TurboTax and other major software definitely handle gambling income, but they don't analyze your documents to identify which transactions are gambling-related versus other types of income. You still have to manually figure that out and enter everything correctly. Taxr.ai does that analysis automatically, which saved me hours of sorting through transactions and reduced my stress about making mistakes.

How does Claimyr actually work? I thought it was impossible to get through to the IRS without waiting for hours. Seems sketchy that they can somehow jump the line when nobody else can.

This sounds like BS honestly. If it actually worked, everyone would use it and the IRS would shut it down. They're probably just selling your info or something.

It uses a system that continually redials the IRS using multiple lines until one connects, then transfers that connected call to you. It's completely legitimate - they don't access any of your tax info or speak to the IRS on your behalf. They just get you connected directly to an agent. The IRS actually doesn't mind because it helps distribute calls more efficiently rather than having thousands of people all manually redialing and clogging up the system. They've been featured in major news outlets and they're transparent about how the service works - nothing sketchy about it.

That's what I originally thought too! But from what I've experienced, BetMGM only issues W-2G forms for certain types of big wins (like jackpots over $1,200 or wins with odds of 300-to-1 or higher). My situation was more about accumulated smaller wins over time, which is why I was concerned about the PayPal/Venmo reporting.

That makes sense. The rules vary by type of gambling. Slots and certain casino games use that $1,200+ threshold, while poker tournaments use $5,000+ winnings. For sports betting specifically, they generally only issue W-2Gs when the win is both over $600 AND at least 300x the wager amount. So most typical sports bettors won't get W-2Gs even with decent winnings, which is probably why the payment app reporting became a bigger concern. Thanks for clarifying your situation!

I asked my tax guy about this last year. He said ideally you should keep a "session log" for each day you gamble. Record your starting and ending amounts for each session rather than every single bet. The IRS considers a "session" to be your gambling activity for a single day at a single establishment or site.

This is really helpful advice! I'm wondering about the reconciliation part you mentioned - if I do get a 1099-K from Venmo showing gross payments, how exactly do I show the IRS that some of those payments were just transfers between my own accounts versus actual gambling income? Do I need to provide bank statements or is there a specific form for that? Also, when you say "gambling log by session," does that mean I need to go back and recreate records for this past year, or is it too late for that? I've been pretty casual about tracking until now but this thread is making me realize I need to get more organized!

@NeonNebula Great questions! For reconciling a 1099-K, you'd typically attach a statement to your tax return explaining the discrepancy. Something like "1099-K shows $X gross payments, but only $Y represents taxable gambling winnings. Remaining $Z were transfers between personal accounts." Keep your bank statements, payment app transaction histories, and gambling site records as backup documentation. As for recreating records - it's not too late! Most online sportsbooks like BetMGM keep detailed transaction histories you can download. PayPal and Venmo also provide transaction exports. You can reconstruct your gambling log by matching deposits/withdrawals between platforms. The IRS accepts reconstructed records as long as they're reasonable and well-documented. Pro tip: Going forward, consider using a simple spreadsheet with columns for Date, Platform, Starting Balance, Ending Balance, and Net Win/Loss. Takes just a minute after each session and will save you hours during tax season!

Great question about net losses! Even if you had an overall net loss for the year, you still need to report your total winnings as income on your tax return. The losses can only offset the winnings - you can't use gambling losses to reduce other types of income or create a net negative. So if you won $5,000 total but lost $7,000 total during the year, you'd report $5,000 as gambling income and then deduct $5,000 in gambling losses (not the full $7,000). The remaining $2,000 in losses essentially disappears for tax purposes. Regarding audits, I haven't been audited personally, but I work in tax preparation and have seen a few gambling-related audits. The IRS typically wants to see detailed records of both wins and losses - betting platform statements, bank records, and ideally a gambling diary or log. They're particularly interested in making sure people aren't claiming losses without corresponding winnings to offset them. Having good documentation from platforms like Caesars, Cash App, and your bank accounts should be sufficient as long as the records clearly show the gambling activity timeline and amounts.

You've done a great job summarizing the key points from this discussion! Regarding taxr.ai, from what I understand it works by analyzing uploaded transaction files rather than direct integration with betting platforms. So you'd download your statements from BetMGM, PayPal/Venmo, and your bank, then upload those files for analysis. For someone with a straightforward situation like yours, a well-organized spreadsheet might be sufficient. But if you're dealing with multiple platforms, frequent transactions, or complex money movements between different accounts, the automated categorization could definitely save time and reduce errors. I'd also be curious to hear from @Jamal Thompson about BetMGM s'year-end reporting. Most major sportsbooks do provide some kind of annual summary even if they don t'issue formal tax documents. Having that official summary from the source platform makes record-keeping much easier and more credible if questions ever arise. The peace of mind factor is worth considering too - knowing you ve'properly categorized everything and haven t'missed any deductible losses can be worth the cost of a service, especially if your betting activity was substantial this year.

@Saanvi Krishnaswami Really excellent point about state-specific requirements! I hadn t'even thought about that aspect. I m'in New Jersey where sports betting has been legal for a while, but you re'absolutely right that newer states might have different rules or additional reporting requirements that could complicate things. The email confirmation tip is brilliant too. I just went back and found dozens of DraftKings and FanDuel confirmation emails that I had completely forgotten about. Some of them show different amounts than what I remembered, so this could definitely help people who are trying to reconstruct their records accurately. Your point about timing is also really important - I had a few bets that I placed in December 2023 but the winnings weren t'credited until January 2024. For tax purposes, those would count toward 2024 income, not 2023, even though I placed the bets in the previous year. That kind of detail could definitely matter if someone is trying to figure out which tax year to report certain income. This whole discussion has made me realize how complex sports betting taxation can be, especially when money moves through multiple platforms. Thanks for adding these practical insights!

@Laura Lopez This is such great advice about taking screenshots of annual summaries! I wish I had known this earlier in the year. I just checked my BetMGM account and they do have a Year-End "Summary section" that shows my total activity, but like you said, the detailed transaction history only goes back about 15 months. Your point about the master spreadsheet is spot on too. I ve'been tracking each platform separately and just realized I might be making this way more complicated than it needs to be. Having everything in one consolidated view would definitely make it easier to see the big picture and catch any discrepancies. One thing I m'curious about - when you mention not double-counting transfers between platforms and payment apps, do you have a specific system for flagging those transactions? I m'worried I might accidentally report the same money as income when it moves from ESPN BET → Venmo → Bank account, since each platform shows it as a separate transaction. This thread has been incredibly helpful for someone like me who s'new to navigating sports betting taxes. The real-world experiences and practical tips from everyone are way more valuable than the generic advice you find on most tax websites!