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This entire discussion has been a goldmine of practical information! I'm jumping in as someone who just took over as treasurer for our local community center that runs quarterly raffles for building maintenance funds. After reading through all these detailed responses, I'm realizing we've been flying blind on tax compliance. We've had a few winners over $1,000 in the past year and honestly never thought about issuing any tax forms. This thread is both eye-opening and slightly terrifying! The clarity everyone provided on the W-2G vs 1099-MISC distinction is incredibly helpful. I was completely unaware that there were different forms for different prize scenarios. The bundle ticket pricing calculation that @Giovanni Colombo mentioned is something I definitely would have calculated wrong - we do 5 tickets for $20 deals regularly. I'm definitely going to look into the taxr.ai tool that @Amina Diallo recommended. Having something analyze our raffle structure and tell us exactly which forms we need sounds like a huge time-saver, especially since I'm learning all this as a volunteer with a full-time day job. Also adding Claimyr to my list after seeing the success stories from @Javier Cruz and @Malik Thomas. The IRS phone system has been my nemesis when trying to get answers about our 990-EZ filings. Quick question: for our upcoming spring raffle, we're planning a $5,000 grand prize with $25 tickets. Based on everything discussed here, that would definitely require a W-2G (over $600 and 200x the wager), plus the 24% withholding that @NeonNebula mentioned, correct? Want to make sure I understand before we finalize our prize structure. Thank you @Keisha Johnson for asking this question and everyone for sharing such detailed, practical guidance!
@Katherine Hunter Yes, you re'absolutely correct! With a $5,000 grand prize and $25 tickets, that s'exactly 200x the wager amount, so you d'definitely need to issue a W-2G to the winner. And since it s'over the $5,000 threshold, you ll'need to withhold 24% federal income tax before distributing the prize. So the winner would actually receive $3,800 $5,000 (- $1,200 withholding ,)and you d'need to deposit that $1,200 with the IRS. The winner gets credit for the withholding when they file their tax return. Don t'forget to get the W-9 form completed before you hand over any money! And you re'smart to figure this out before finalizing your prize structure - much easier than scrambling to understand the requirements after you ve'already drawn the winner. Welcome to the world of raffle tax compliance! It seems overwhelming at first, but once you get the systems in place, it becomes much more manageable. This thread has been such a great crash course for all of us dealing with these requirements. The tools everyone mentioned really do help - having that guidance takes a lot of the guesswork out of compliance for volunteer treasurers like us who are juggling this alongside everything else!
This has been such an incredibly thorough and helpful discussion! As someone who just joined the board of a small food pantry that's planning to add raffles to our fundraising mix, I feel like I've gotten a complete education in charitable gaming compliance just from reading through everyone's experiences. The practical advice shared here is exactly what small nonprofits need - real examples with specific dollar amounts, actual tools that work, and lessons learned from mistakes. I especially appreciate how @Paolo Longo broke down the W-2G vs 1099-MISC distinction so clearly, and how multiple people confirmed the approach with their own experiences. A few things I'm definitely implementing based on this thread: - Creating a "winner packet" with W-9 forms and tax explanation materials (thanks @Mia Green!) - Checking our state's charitable gaming license requirements before we launch - Using the effective ticket price for any bundle pricing in threshold calculations - Setting up proper record-keeping systems from day one The tool recommendations are going straight to my resource list. As a volunteer handling compliance alongside a full-time job, having services like taxr.ai to analyze requirements and Claimyr to actually reach IRS agents sounds invaluable. @Keisha Johnson - thank you for asking such a practical, detailed question that sparked this amazing knowledge-sharing session. Your specific prize amounts and ticket pricing gave everyone concrete examples to work with rather than abstract concepts. One follow-up question: for organizations just starting with raffles, would you recommend running a small "test raffle" first (maybe keeping prizes under reporting thresholds) just to get comfortable with the administrative side before scaling up? Or is it better to just dive in with proper systems from the start? This community is such a great resource for nonprofit volunteers trying to navigate these regulatory requirements while focusing on our charitable missions!
As someone completely new to both this community and the world of lottery taxation, I have to say this thread has been absolutely incredible for understanding the harsh reality of how winnings actually work! The most shocking revelation for me has been learning that a "$2 million" jackpot advertised everywhere might only put around $700k in your actual bank account. That's just mind-boggling, but I'm so grateful to learn this now rather than potentially being caught off guard later. What really gets me is how that automatic 24% federal withholding seems to give people this false confidence that most of their tax obligation is handled. Reading all the real-world examples shared here - @Kingston Bellamy going from $25k to $16k take-home, @AaliyahAli's brother getting hit with penalties, and others - really shows how that withholding is just the beginning, not the end. The consistent advice from everyone about immediately setting aside 50% of any winnings and not touching the money for months makes total sense now. It seems like the only way to protect yourself from getting blindsided when the full tax reality hits at filing time. I'm also bookmarking all the resource recommendations mentioned throughout this discussion - taxr.ai for accurate tax calculations and Claimyr for actually getting through to the IRS when you need answers. Having professional tools to navigate this complexity rather than just hoping for the best seems absolutely essential. This whole conversation really makes me think lottery advertising should be required to show realistic take-home amounts instead of just those eye-catching jackpot numbers that are essentially meaningless. Thanks to everyone for sharing their experiences and hard-learned lessons - this has been like getting a crash course in lottery taxation that should honestly be required reading before anyone buys a ticket!
@Dylan Wright, this thread has been such an incredible education for all of us newcomers! Your summary really captures how eye-opening this whole discussion has been. What strikes me most is how the lottery system seems almost intentionally designed to mislead people. That gap between the "$2 million" on the billboard and the actual $700k you might see is just staggering. And you're absolutely right about that 24% withholding creating false confidence - it's like they're giving you a taste of what taxes feel like while the real bill is waiting around the corner. All the real experiences shared here have been invaluable. Hearing from people like @Kingston Bellamy and learning about @AaliyahAli's brother's situation really drives home that this isn't just theoretical - these tax complications hit real people hard when they're not prepared. The 50% rule everyone keeps mentioning is definitely going in my mental playbook. Better to be overly cautious and have money left over than to get caught short when tax time comes around. Your point about advertising reform really resonates with me too. It feels like there should be some kind of consumer protection requiring realistic disclaimers about take-home amounts. Those giant jackpot numbers are essentially marketing fiction without proper context. Thanks for such a thoughtful wrap-up of everything we've all learned here!
As a complete newcomer to this community, I have to say this discussion has been absolutely eye-opening! I stumbled upon this thread while trying to understand lottery taxation myself, and honestly had no idea how complex and brutal the reality actually is. The fact that a $2 million advertised jackpot could realistically end up being around $700k in your pocket is just staggering. But what's even more concerning is how that 24% automatic withholding seems designed to give winners a false sense of security about their tax situation. Reading through everyone's real experiences here - from @Kingston Bellamy's $25k win netting only $16k to @AaliyahAli's brother facing unexpected penalties - really drives home how the initial withholding is just scratching the surface of your actual tax obligations. The consistent advice about immediately setting aside 50% of any winnings and not touching the money for months is clearly the wisdom of experience speaking. It seems like the only safe approach given how many layers of taxation and complexity are involved. I'm definitely bookmarking the resource recommendations mentioned throughout this thread too. Having professional tools like taxr.ai and services like Claimyr to navigate this maze rather than trying to figure it out alone seems absolutely crucial. This whole conversation really makes me think there should be truth-in-advertising requirements for lottery marketing. Those massive jackpot numbers are essentially meaningless without proper context about what winners actually receive. Thanks to everyone who shared their hard-learned lessons - this has been incredibly educational!
Just finished dealing with one of these for my 2022 return! They questioned some charitable contributions. I sent donation receipts, bank statements showing the transfers, and a spreadsheet summarizing everything. Got confirmation last week that my return was accepted as filed. The whole process took about 10 weeks from first letter to resolution. Just be methodical and you'll be fine!
I just went through something similar! Got a "tax review" letter in January for my 2023 return - they were questioning my business expense deductions. Turned out to be a CP75 correspondence examination, which is basically their way of saying "prove this one thing and we'll leave you alone." The vague language is definitely frustrating, but here's what worked for me: I called the number on the letter (took 3 attempts over different days to get through), and the agent was actually helpful in explaining exactly what they needed. They were specifically reviewing my office supply and travel expenses because the amounts were higher than typical for my industry. Sent them organized receipts, bank statements, and a simple spreadsheet showing the business purpose for each expense. Got a "no change" letter about 7 weeks later. The whole thing was much less scary than it seemed initially - just their way of spot-checking specific items that their computers flagged. Your straightforward situation will probably resolve even faster than mine did!
Thanks for sharing your experience! It's really reassuring to hear from someone who just went through this. Did you have to provide documentation for every single business expense, or were they focused on specific categories? I'm trying to figure out if I should prepare everything or wait to see what they specifically ask for in their follow-up correspondence.
Has your wife checked if you're accidentally claiming some deduction or credit that's a major audit trigger? For years I kept getting letters because I was mixing up the American Opportunity Credit and Lifetime Learning Credit for my kids' education expenses.
I've been through this exact same frustrating cycle! Got audited three years in a row before figuring out what was happening. In my case, it turned out to be a combination of two issues: my employer kept making small errors on my W-2 (like reporting $52,347 instead of $52,374) and I was inconsistently rounding numbers on my return. The IRS computer systems are incredibly sensitive to mismatches. Even if your actual tax liability is correct, any discrepancy between what you report and what third parties (employers, banks, etc.) report to the IRS can trigger verification requests. Here's what finally helped me: I started pulling my wage and income transcripts from the IRS website BEFORE filing my return to see exactly what information they already had on file. Then I made sure my return matched those numbers precisely - no rounding, no "close enough" estimates. Also worth noting - if you've moved recently or changed jobs, make sure all your addresses are consistent across all forms. The IRS uses address matching as one way to verify identity, and any inconsistencies can flag your return for additional review. Since making these changes, I haven't had a single audit or verification request in over four years. Sometimes it really is just about being more precise with the details rather than anything being fundamentally wrong with your return.
This is incredibly helpful advice! I never thought about pulling the wage and income transcripts beforehand to check what the IRS already has on file. That's such a smart way to avoid mismatches. Do you know roughly how long before filing season those transcripts become available? I want to make sure I can access them early enough to compare before we prepare our return.
Lucas Bey
This happened to me too! The stress is real when you're waiting that long for your refund š° Everyone's right about the Form 8822 - that's absolutely your first step. But also wanted to add that you can check your refund status online at irs.gov using "Where's My Refund" tool. It'll show if there are any issues or if they're trying to send it to the wrong address. Also, if you have access to your old mailbox (like if you're still friendly with new residents/landlord), might be worth giving them a heads up to watch for any IRS mail just in case. The whole system is definitely frustrating but hang in there!
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Harmony Love
ā¢@Lucas Bey Great advice about checking Where "s'My Refund online!" I totally forgot about that tool - it actually shows you if there s'an address issue or if the refund got sent back. And yeah, definitely reach out to whoever s'at your old place if possible. When I moved last year I gave my old landlord my new address just for situations like this. The whole IRS system is so outdated but at least there are ways to track what s'happening. Thanks for the reminder about the online tool!
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Hiroshi Nakamura
Just went through this nightmare myself! Filed Form 8822 back in November when I moved and STILL had issues with my refund going to the old address in January š¤¦āāļø The IRS systems don't talk to each other apparently. Had to call that hotline like 5 times before someone finally noted my case and reissued the check. Definitely file the form ASAP but also call them directly - sometimes the form takes weeks to process and your refund could get sent out before they update your address in their system. So frustrating but you'll get through it! The reissued check only took about 3 weeks once they actually processed my address change.
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Javier Mendoza
ā¢@Hiroshi Nakamura Wow that s'so frustrating that even filing the form in advance didn t'prevent the issue! š¤ Thanks for the heads up about calling them directly too - sounds like the phone route might be faster than waiting for the paperwork to go through their system. Did you have to provide any specific info when you called to get them to actually note your case? I m'definitely going to try both approaches now after reading everyone s'experiences here!
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