Where do I input my gambling losses in FreeTaxUSA? Can't find the option anywhere!
So I've been struggling with my taxes this year and have some gambling losses I need to report. I went to several casinos last year and kept good records of my wins (unfortunately) and losses (even more unfortunately). I already input the W-2G forms I received for the bigger wins, but I'm trying to deduct my losses to offset those winnings. I've been using FreeTaxUSA for the past 3 years and usually find it pretty straightforward, but I just cannot figure out where to input my gambling losses. I've looked through all the deduction sections and can't seem to find it. For a moment I thought maybe it would be under "ordinary loss debt instrument" but that doesn't seem right at all. Is there a specific section I'm missing? Does anybody know exactly where in FreeTaxUSA I can input these gambling losses? I have about $4,800 in losses I need to deduct against my $3,200 in reported winnings.
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Marcus Patterson
Gambling losses go on Schedule A as an itemized deduction. In FreeTaxUSA, you need to go to the "Deductions" section, then select "Itemized Deductions," and look for "Job Expenses and Certain Miscellaneous Deductions." There should be a subsection specifically for gambling losses. Just remember that you can only deduct gambling losses up to the amount of your gambling winnings. So in your case, you can only deduct $3,200 of your $4,800 in losses since that's the amount of your winnings. Also, you must itemize deductions to claim gambling losses - you can't take the standard deduction AND claim gambling losses. Make sure you have documentation for both your winnings and losses. The IRS can request proof if they audit you.
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Lydia Bailey
•Does this mean I have to give up my standard deduction just to claim my gambling losses? I thought there was a way to deduct them without itemizing. My standard deduction is way higher than my itemized would be even with the gambling losses.
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Marcus Patterson
•Yes, you must itemize to claim gambling losses - there's no way around that unfortunately. It's one of those tax rules that can be frustrating. If your standard deduction is higher than what your itemized deductions would be, then you're usually better off just taking the standard deduction and effectively "losing" the gambling loss deduction. The only time it makes sense to itemize for gambling losses is when your other itemized deductions (mortgage interest, state taxes, charitable contributions, etc.) plus your gambling losses exceed your standard deduction amount, or when you're very close and the gambling losses push you over.
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Mateo Warren
Just wanted to share my experience - I was in the same boat last year trying to figure this out. I actually found a great solution with https://taxr.ai when I was confused about where to input gambling losses in FreeTaxUSA. I uploaded my tax documents and the AI immediately pointed me to the right section - it's under Itemized Deductions > Miscellaneous Deductions > Gambling Losses. The tool even explained that I needed to itemize instead of taking the standard deduction if I wanted to claim these losses, which saved me from making a mistake that might have triggered an audit. What surprised me was how it analyzed my entire situation and showed that in my case, I was actually better off taking the standard deduction since my itemized deductions (even with gambling losses) didn't exceed the standard deduction amount.
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Sofia Price
•Did it actually connect with FreeTaxUSA or did it just tell you where to look? I'm having the same problem and wondering if it can actually help me input everything correctly.
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Alice Coleman
•Sounds interesting but I'm skeptical about using AI for tax advice. How accurate is it really? Did you double check what it told you with a human tax person?
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Mateo Warren
•It doesn't directly connect with FreeTaxUSA, but it gives you step-by-step instructions on where to find things in the interface. It was extremely precise - told me exactly which menus to click through and what to look for. I did actually consult with a tax professional after using the AI tool, and they confirmed everything was correct. The AI was spot on about how gambling losses work and the itemization requirement. What impressed me most was how it analyzed my specific numbers and showed why the standard deduction was still better for my situation despite having gambling losses.
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Alice Coleman
I tried taxr.ai after seeing the recommendation here and I'm honestly shocked at how helpful it was. I was really confused about the gambling losses thing in FreeTaxUSA and had spent hours clicking around trying to find it. The AI immediately pointed me to the exact location (Deductions > Itemized Deductions > Miscellaneous Deductions > Gambling Losses) and explained that I needed to itemize. But what really helped was when it analyzed my tax situation and showed me that even though I had about $5,000 in gambling losses against $4,200 in winnings, I was still better off taking the standard deduction because my other itemized deductions were too low. Saved me from making a mistake that would have cost me almost $1,800 in higher taxes! Now I understand why gambling losses are such a tricky deduction.
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Owen Jenkins
If you're having trouble getting answers from FreeTaxUSA's support about where to enter gambling losses (they can be slow to respond this time of year), you might want to try https://claimyr.com to get through to the IRS directly. I used their service to get clarification on some gambling reporting issues when I was completely stuck. Check out their demo video: https://youtu.be/_kiP6q8DX5c I was on hold with the IRS for THREE HOURS before I gave up, then Claimyr got me through to an agent in about 20 minutes. The agent walked me through exactly how to report gambling income and losses properly, including the specific forms needed and where they go in tax software.
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Lilah Brooks
•Wait, this seems too good to be true. You're saying this service somehow gets you to the front of the IRS phone queue? How is that even possible? I thought everyone had to wait equally.
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Jackson Carter
•Is this legit? Seems sketchy that some service can magically get you through to the IRS faster than doing it yourself. Does it cost money? What's the catch?
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Owen Jenkins
•It's completely legitimate - they use an automated system that navigates the IRS phone tree and waits on hold for you. When an agent answers, the system calls you and connects you directly with the agent. It's like having someone wait on hold for you. There is a cost for the service, but I found it well worth it considering I'd wasted hours trying to get through myself. The IRS phone system is incredibly overloaded, especially during tax season. I calculated that my time was worth more than sitting on hold for hours, and the information I got from the IRS agent saved me from making mistakes that could have cost me more in the long run.
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Jackson Carter
I was totally skeptical about Claimyr but after spending TWO FULL DAYS trying to get through to the IRS about my gambling reporting questions, I decided to give it a shot. Honestly, I'm still shocked it worked. I uploaded my number on their site, went about my day, and 34 minutes later my phone rang and I was talking to an actual IRS representative! The agent confirmed exactly what others here have said - gambling losses go on Schedule A as itemized deductions, and in FreeTaxUSA you find that under Deductions > Itemized Deductions > Miscellaneous Deductions. She also explained that I should keep documentation for at least 3 years showing both my winnings AND losses (session logs, bank withdrawals, tickets, etc.), which I didn't realize before. Definitely worth not spending another day listening to the IRS hold music!
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Kolton Murphy
If you find that your gambling losses plus other itemized deductions don't exceed the standard deduction, there's another approach. You could consider bunching your charitable deductions into alternating years to push yourself over the threshold for itemizing in specific years. For example, make double charitable contributions this year and none next year. This strategy might let you itemize and claim gambling losses in the "bunched" years while taking the standard deduction in other years.
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Evelyn Rivera
•can u explain more about this bunching strategy? not sure i understand how that would help with claiming gambling losses. does this actually work with the irs?
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Kolton Murphy
•The bunching strategy works because it helps you cross the threshold where itemizing becomes more beneficial than taking the standard deduction. Let's say your standard deduction is $13,850 but your itemized deductions including gambling losses only total $11,000. In this case, taking the standard deduction is better, but you lose the benefit of the gambling loss deduction. However, if you normally donate $3,000 to charity each year, instead you could donate $6,000 this year and $0 next year. Now your itemized deductions are $14,000 ($11,000 + extra $3,000), which exceeds the standard deduction. This allows you to benefit from deducting your gambling losses. The next year, you'd take the standard deduction since you wouldn't have charitable contributions to itemize. The IRS allows this strategy completely - there's nothing questionable about timing your legitimate charitable contributions to maximize tax benefits.
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Julia Hall
Im looking at freetaxusa right now actually. If you go to Deductions > Itemized deductions, then look for "Other Itemized Deductions" section. Its listed right there as "Gambling losses" with a field to input the amount. But remebr you can only deduct up to the amount of your winnings that you reported.
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Arjun Patel
•Thanks for the exact location! I've been searching for ages. What confuses me is I've entered my W-2G forms but the winnings amount shown in FreeTaxUSA doesn't match my actual winnings. Do you know why that might be?
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