Winning at online blackjack - how do I report gambling winnings on taxes?

So if I'm understanding right, I report the full amount of winnings but can only deduct losses if I itemize? What if my total winnings for the year is relatively small like $500? Do I still need to report that?

Yes, you need to report ALL gambling winnings regardless of the amount. The IRS considers even small amounts like $500 to be taxable income. As for deducting losses, that's correct - you can only deduct gambling losses if you itemize deductions on Schedule A instead of taking the standard deduction. For most people, the standard deduction ($13,850 for single filers in 2024) is higher than their itemized deductions would be, so they're better off taking the standard deduction and not deducting gambling losses. But if you have other significant deductions like mortgage interest or large charitable donations that make itemizing worthwhile, then you can include your gambling losses as well.

How does it work with the Excel sheets? Do you just upload them directly or do you have to format them in a specific way first? My tracking is kinda messy.

Is this just for gambling stuff or does it work for other types of income too? I do some freelance work besides my online poker and wondering if it could help with all of it together.

You can upload Excel sheets directly - the system is pretty smart about recognizing different formats. I uploaded my messy tracking sheets without any special formatting and it figured everything out. It actually helped me organize my records better for next year too! As for other income types, it definitely handles multiple income streams. I used it for both my gambling income and some consulting work I did. It separates everything appropriately and makes sure you're applying the right tax treatment to each type of income. Really helpful if you have both gambling and freelance/1099 work since they're taxed differently.

Wait how does this actually work? Does someone else talk to the IRS for you? Seems weird they'd discuss your tax info with someone else.

Yeah right. So you're telling me there's some magical service that somehow jumps the IRS phone queue? I've waited HOURS multiple times. If this actually worked, everyone would be using it. Sounds like BS to me.

No one talks to the IRS for you - they just hold your place in line. When an IRS agent finally answers, you get a call connecting you directly to them. Your tax info stays private between you and the IRS agent. I had the exact same reaction you did! I spent 2+ hours on hold with the IRS last April and finally gave up. When I found Claimyr, I figured it had to be a scam. But I was desperate enough to try it, and I got connected to an IRS agent in about 45 minutes without having to stay on the phone the whole time. They just call you when someone picks up. I think it works because most people don't know about it yet. It's definitely real - I even got the agent's ID number and everything so I could reference the call in my records.

Thanks for bringing this up! My tracking spreadsheet just has deposits and withdrawals with dates, but not broken down by actual playing sessions. If I play multiple times in one day, do I need to track each individual session or can I just track by day?

Each distinct playing session should be tracked separately, even if they occur on the same day. The IRS considers a session to end when you stop playing a particular game for a significant period. For online gambling, a good rule of thumb is that if you log out or stop playing for several hours, that ends a session. If you play blackjack for an hour, take a break for several hours, then play again, those would be two separate sessions. Some tax professionals recommend documenting the start and end times of each online gambling session to make this clear. The more detailed your records, the better position you'll be in if questions ever come up.

This is true! The IRS has reporting requirements for banks too. Any deposit over $10k gets automatically reported, and they also look for patterns of smaller deposits that might be trying to avoid that threshold. Plus with the new reporting for payment apps like Venmo and PayPal, there's a lot more visibility into money movement than people realize.