Need help calculating my gambling winnings for tax purposes

Congrats on your wins! Yes, you need to report all gambling winnings on your taxes, even if you didn't receive a W-2G form for every win. The IRS requires you to report all gambling income regardless of whether you received a tax form. For your blackjack winnings, even though you didn't get a W-2G, that $7,500 is still taxable income. The casino only issues W-2Gs for certain games and when winnings exceed specific thresholds (which is why you got one for the slots). You can absolutely deduct your gambling losses, but there's a catch - you can only deduct losses up to the amount of your winnings, and you must itemize deductions on Schedule A rather than taking the standard deduction. Make sure you keep good records of both your winnings and losses (receipts, tickets, bank withdrawals, etc.).

After reading your post, I immediately thought you should check out https://taxr.ai - it seriously helped me with a similar situation last year. I had a mix of poker tournament winnings and some sports betting, and I was totally confused about what to report and how to document my losses. Their system analyzed all my gambling records and explained exactly how to report everything correctly. They even helped me understand how to properly document my losses with a gambling log that would stand up to IRS scrutiny if I ever got audited. The detailed analysis saved me from making mistakes that could have triggered an audit.

Just wanted to update - I actually tried https://taxr.ai after asking about it here. Seriously impressed! I uploaded my W-2G from the slots and entered my blackjack winnings manually, and it organized everything perfectly. The gambling log template they provided made tracking my losses so much easier than the spreadsheet mess I was trying to create. The best part was the explanation of whether itemizing made sense for my situation. Turns out with my mortgage interest and charitable donations added to the gambling losses, itemizing was actually better than the standard deduction by about $3,000. That's a tax savings I would have missed! If you're dealing with gambling winnings, definitely worth checking out.

If you're having trouble getting through to the IRS about gambling tax questions (which is likely since their phone lines are a nightmare), try using https://claimyr.com to get a callback. I spent days trying to reach someone at the IRS to clarify some questions about documenting my casino winnings. With Claimyr, I got a callback in under 2 hours when I had been trying for literally weeks on my own. Here's a video showing how it works: https://youtu.be/_kiP6q8DX5c. The IRS agent I spoke with gave me specific guidance on how to document my gambling activities properly and what would be acceptable proof if I was ever audited.

I need to eat my words. After posting my skeptical comment, I was desperate enough to try Claimyr because I had some specific questions about reporting my poker tournament winnings. Not only did I get a callback from the IRS within 90 minutes, but the agent I spoke with was actually helpful and walked me through exactly how to document my situation. The agent confirmed that I needed to keep a detailed log of all sessions (date, location, type of gambling, amounts won/lost) and that ATM receipts at casinos could help establish my presence there on specific dates. He also explained that I could use my player's card records as supporting documentation. This was information I couldn't find anywhere online. Sometimes you need to talk to an actual human at the IRS, and this service made that possible when I thought it was impossible.

Make sure you're tracking sessions, not individual hands/plays! Common mistake I see people make with gambling taxes. Each "session" (continuous period of play) can be considered one unit for tax purposes. So if you play blackjack for 3 hours, leave, then come back later, that's 2 sessions. Don't try to claim each hand as a separate win/loss.

Has anyone used TurboTax for reporting gambling winnings? Does it walk you through the process well or should I use a different tax software?

One thing I'd add that hasn't been mentioned yet - keep ALL your receipts from the casino, not just the W-2G forms. This includes ATM receipts, food/drink receipts, parking receipts, even hotel receipts if you stayed overnight. These help establish a timeline and can support your gambling activity documentation. Also, consider opening a separate bank account just for gambling if you plan to do this regularly. It makes tracking so much easier come tax time. You deposit your gambling bankroll, withdraw winnings, and everything is cleanly separated from your regular finances. And remember - gambling winnings are subject to both federal AND state taxes in most states, so don't forget to check your state's specific requirements. Some states have different thresholds for reporting than the federal government.