Do I need to report my $4,800 50/50 raffle winnings on my taxes?

Yes, you'll need to report this as gambling winnings on your tax return, even though it's under $5,000. The organization should provide you with a Form W-2G if the amount is $600 or more, which your winnings definitely qualify for. Even if they don't send you a form for some reason, you're still legally required to report these winnings. The forms you filled out were likely to collect your information for tax reporting purposes, not actual W-2 forms (those are for employee wages). Since no taxes were withheld, you'll want to set aside some money to cover the taxes due. The exact amount depends on your overall income and tax bracket, but planning for 20-25% of the winnings is generally a safe estimate. You'll report this on Schedule 1 of your Form 1040 when you file next year. The good news is you can also deduct gambling losses if you itemize deductions on Schedule A, but only up to the amount of your winnings.

I went through almost the exact same situation last year! After spending hours researching and stressing about it, I found this AI tax assistant at https://taxr.ai that saved me so much headache. You upload your documents and it tells you exactly what forms you need and how to report everything. For gambling winnings like yours, it explained that I needed to report it on my 1040 form even though it was under $5k, and showed me exactly where to put the info. It also helped me understand what documentation I needed to keep just in case. Definitely made me feel more confident that I wasn't missing anything.

Just wanted to follow up - I finally tried taxr.ai after dealing with an unexpected inheritance situation. The whole process was super straightforward. I uploaded the statements I had, and it immediately identified what needed to be reported where. It even flagged that I might be eligible for a special deduction related to some of the inheritance taxes I'd already paid that I had no idea about. The step-by-step guidance made me actually understand what I was filing instead of just blindly following prompts like with other services. Definitely going to use it for my regular taxes next year too!

Just a heads up - if you need to talk to someone at the IRS about how to properly report this (which I recommend), good luck getting through on the phone. After my casino winnings last year, I spent DAYS trying to get through to a human. Found this service called Claimyr at https://claimyr.com that got me connected to an IRS agent in about 20 minutes instead of the endless hold times. They have a demo video at https://youtu.be/_kiP6q8DX5c showing how it works. The IRS agent I spoke with was actually super helpful and explained exactly how to report my winnings and what documentation I needed to keep. Definitely worth the call since my situation had some complications that online guidance couldn't fully address.

I'm back to eat my words. After seeing a couple more people mention Claimyr on another thread, I broke down and tried it when I needed to ask about an amended return problem. Fully expected to waste my money, but holy crap it actually worked. Got a call back in about 30 mins and was talking to a real IRS person. The agent looked up my account and found that my amended return from last year was stuck in processing limbo. She put in some kind of note on my account to have it reviewed again. Probably saved me months of waiting and wondering if they'd ever process it. Honestly still shocked this actually worked.

Don't forget about state taxes too! Depending on what state you live in, you might need to report the gambling winnings on your state income tax return as well. Some states fully tax gambling winnings while others have different rules.

Just curious, was this a charity raffle? If it was for a qualifying charity event, you might be able to deduct a portion of the ticket cost as a charitable contribution (the part that exceeds the fair market value of what you won). Doesn't offset the winnings fully but might help a little bit.

You might also want to check if you need to make an estimated tax payment this quarter rather than waiting until tax time. If you're normally a W-2 employee who gets refunds, you're probably fine waiting. But if this pushes your tax due over $1k for the year beyond what's being withheld, you might need to make an estimated payment to avoid an underpayment penalty.

Congratulations on your win! You've gotten some great advice here already. Just to add a bit more clarity - yes, you absolutely need to report this as "Other Income" on your tax return regardless of whether you receive a W-2G form or not. One thing I'd suggest is opening a separate savings account and immediately putting aside 25-30% of your winnings ($1,200-$1,440) for taxes. This covers both federal and state obligations and gives you a small buffer. It's much easier to do this now while you have the full amount than to scramble for tax money next April. Also, start keeping a simple log of any gambling activities for the rest of the year - both wins and losses. Even if you just buy a few lottery tickets or play bingo, track it all. If you itemize deductions, those losses can offset your winnings dollar-for-dollar up to the amount you won. The IRS considers all gambling winnings taxable income from dollar one, so there's no minimum threshold for reporting requirements on your end, even though there are thresholds for when organizations must issue forms to you.