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Just wanted to chime in as someone who went through a similar situation last year. You're definitely doing the right thing by reporting this - I made the mistake of initially thinking I could "wait and see" if the IRS noticed, but after doing more research I realized that was a terrible idea. One thing I learned that might help you: even though you didn't get a W-2G from DraftKings, they likely have detailed records of your account activity that could be shared with the IRS if requested. Online gambling platforms are subject to various reporting requirements, especially for accounts with significant activity like yours. I'd also recommend keeping a spreadsheet or log of all your gambling activities going forward - dates, sites, amounts wagered, wins/losses, etc. It makes tax time so much easier and gives you solid documentation if you ever face questions from the IRS. For this year's filing, definitely report the full $24k net profit on Schedule 1. Whether itemizing to deduct your losses makes sense depends on your other deductions, but at least you'll have reported the income correctly. Good luck with everything!
This is such helpful advice about keeping detailed records! I'm curious - when you say DraftKings likely has detailed records that could be shared with the IRS, do you know if there's a specific trigger that would cause them to share that information? Is it just during audits, or do they proactively report certain account activities? I want to make sure I understand all the ways the IRS might already know about gambling winnings even without receiving official tax forms.
Great question! From what I understand, gambling platforms like DraftKings share information with the IRS through several mechanisms. They're required to file Currency Transaction Reports (CTRs) for certain large transactions, and they also maintain records that can be requested during IRS investigations or audits. Additionally, under the Bank Secrecy Act, they have to report "suspicious activity" which can include unusual patterns of large wins or deposits. Your $29k win might not trigger automatic reporting, but if the IRS ever decides to audit gambling income or investigate large unexplained bank deposits, they can request detailed account histories from the gambling platforms. The key point is that even if they don't proactively report your specific winnings, the records exist and are accessible to the IRS when needed. That's why it's so important to report everything correctly from the start - the IRS has ways to verify gambling income even when no tax forms are issued to the player.
I went through almost exactly the same situation with online poker winnings a couple years ago - won big but no tax forms from the site. Here's what I learned after consulting with a tax professional: You absolutely need to report the full $24,000 net gambling income on Schedule 1 as "Other Income" regardless of not receiving a W-2G. The threshold for casinos to issue W-2G forms is much higher for online platforms, but your reporting obligation starts at $1. For documentation, download and save your complete account history from DraftKings before the end of the tax year - sometimes these records become harder to access later. Also save screenshots of your year-end summary showing total deposits, withdrawals, and net position. One thing that surprised me: my tax preparer explained that large gambling winnings often trigger "lifestyle audits" where the IRS looks at your overall financial picture. They want to see that your reported income can support your spending patterns. So if you made any large purchases or deposits that year, make sure your total reported income (including the gambling winnings) aligns with your bank activity. The penalties for not reporting can be severe - not just the taxes owed but potential fraud charges if they determine it was intentional. With $24k in winnings, you're definitely in territory where the IRS would take notice if they discovered unreported income later.
Zara Malik
β’This is really eye-opening about the "lifestyle audits" - I hadn't considered that angle before! When you mention that the IRS looks at whether your reported income can support your spending patterns, does that include things like credit card payments or just bank deposits? I'm wondering because I used some of my winnings to pay down debt rather than making obvious large purchases. Also, do you know approximately how long the IRS has to initiate one of these lifestyle audits after you file? I want to make sure I keep all my documentation for the right amount of time.
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This situation totally sucks, but there's one workaround nobody's mentioned yet. If one spouse qualifies as a "real estate professional" (750+ hours working on real estate activities + more time than spent on any other job), then the rental properties aren't considered passive activities anymore. This means the $25,000 allowance and the MAGI limitations don't even apply - you could deduct ALL the losses against your regular income. But the catch is you need to materially participate in the rental activities and document everything meticulously. My accountant had me start keeping a detailed log of every hour I spend on property management, repairs, research, etc. It's not easy to qualify, but if one of you is already spending significant time managing your rentals, it might be worth exploring.
That's really interesting! Do both properties have to be managed by the same spouse to qualify? My wife handles one property and I handle the other. Would we both need to meet the 750-hour requirement separately?
For the real estate professional exception to work in your situation, only one spouse needs to qualify as a real estate professional. However, that spouse would need to materially participate in BOTH properties for the losses to be fully deductible. If your wife meets the 750-hour threshold and spends more time on real estate than other employment, but only materially participates in her property (not yours), then only her property would qualify for the exception. Your property would still be subject to the passive activity rules. The key is that the qualifying spouse needs to materially participate in each property you want to claim non-passive losses for.
Dylan Baskin
Has anyone successfully "grouped" their rental properties as a single activity under Reg. 1.469-4? I was reading that this might help with the material participation requirements if you're trying to qualify as a real estate professional.
Lauren Wood
β’Yes, grouping can be super helpful! We did this last year. You need to file a statement with your tax return declaring that you're treating the properties as a single activity. The properties have to have some commonality - like being in the same geographic area or requiring similar management. The benefit is huge - instead of having to materially participate in each property separately (which is 500+ hours per property), you just need to meet material participation for the group as a whole. But beware - once you group them, it's hard to ungroup them later without IRS permission.
Dylan Baskin
β’Thanks, that's exactly what I needed to know! I was worried about meeting the hour requirements for each property individually. Our properties are all in the same county and we manage them similarly, so it sounds like grouping would work for us. One follow-up question - does this grouping election also help with the marriage penalty issue specifically, or just with qualifying for material participation?
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I went through this exact same frustrating experience last year and want to share what finally worked for me. After waiting 4 months for a refund that never came, I filed Form 3911 and got my money within 6 weeks. Here's my step-by-step process that worked: 1. **Find the correct mailing address** - Don't use a generic IRS address. Go to IRS.gov and look up the specific processing center for your state. For joint filers, this is absolutely critical. 2. **Fill out Section I completely** - Make sure every detail matches your original return EXACTLY, including the refund amount down to the cent from line 35a of your 1040. 3. **Both signatures required** - Since you filed jointly, both you and your husband must sign in Section III. This is where many people get delayed. 4. **Use certified mail with return receipt** - Cost me about $8 but gave me peace of mind. You can track delivery online and have proof the IRS received it. 5. **Keep copies of everything** - Take photos of the completed form before mailing and keep your certified mail receipt. The waiting is brutal because the online tools don't update during the trace process. My "Where's My Refund" still showed the old status until literally the day before my replacement refund was deposited. Don't panic if nothing changes online for weeks - that's completely normal. Timeline for reference: Mailed March 10th, delivered March 13th, replacement refund deposited May 1st. Total time from mailing to money: 7 weeks. You WILL get your refund! The Form 3911 process has a very high success rate. Just be thorough with the paperwork and patient with the timeline. Hang in there!
NebulaNinja
β’This is exactly the kind of detailed, step-by-step guide I was hoping to find! Your timeline is really helpful - 7 weeks total sounds reasonable given what others have shared. I'm particularly glad you mentioned that the online tools don't update during the trace process because I would definitely panic if I didn't see any changes for weeks. Your point about making sure the refund amount matches line 35a exactly is something I hadn't thought about. I was planning to use the rounded number I remembered, but I'll go back and check our actual return to get the precise amount. Thanks for sharing your success story - it's giving me the confidence to move forward with this process. Sometimes you just need to hear from someone who's been through it and came out the other side!
I'm dealing with this exact same situation right now and found this thread incredibly helpful! My wife and I filed jointly in February, were supposed to get our refund in April, and it's now July with no money in sight. The IRS keeps saying it was "issued" but our bank has no record of any deposit attempt. I've been hesitant to file the Form 3911 because I wasn't sure about the process, but reading all these success stories has convinced me to move forward. The step-by-step advice about finding the correct service center address, using certified mail, and making sure both spouses sign has been invaluable. One question for those who've been through this - did anyone have to deal with interest or penalties during the refund trace period? I'm worried that while we're waiting for this to get resolved, we might get hit with late payment notices for estimated taxes or other issues. Our refund was supposed to cover our next quarterly payment, so the delay is really throwing off our financial planning. Thanks to everyone who shared their experiences and timelines. It's reassuring to know this process actually works, even though it's frustratingly slow!
Ava Garcia
β’Great question about interest and penalties! I went through this exact situation and can reassure you that you won't be hit with penalties during the refund trace period. The IRS puts a hold on your account while Form 3911 is being processed, so any deadlines that would normally apply get extended. That said, I'd recommend calling the IRS once you get confirmation that they received your Form 3911 (via your certified mail receipt) to make sure they've noted the refund trace on your account. When I called about 2 weeks after mailing mine, the agent confirmed the trace was in progress and assured me there would be no penalty issues while it was being resolved. For your quarterly payment situation, you might want to consider making the payment anyway if you can swing it, just to be safe. Once your refund comes through, you can apply any overpayment to future quarters or request another refund. I know that's not ideal when you're already dealing with missing money, but it might give you peace of mind. The certified mail approach really is worth it - being able to track delivery and know exactly when they received it makes the whole waiting process much less stressful!
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I had to do in-person verification about 8 months ago and honestly it was much easier than I expected! The IRS agent was really patient and professional. A few things that helped me prepare: I made a checklist of all required documents and checked them off as I gathered them, brought everything in a manila envelope to stay organized, and reviewed my last tax return the night before so I could answer any questions about it. The actual verification process was super quick - they just compared my face to my ID, verified my Social Security card was authentic, and asked me to confirm some basic info like my address and filing status. The longest part was actually the wait time, but even that was only about 25 minutes. One tip: if you have any name changes (marriage, etc.), bring documentation for that too just in case. You'll do great! π
Isaac Wright
β’Thanks for the detailed breakdown! The checklist idea is brilliant - I'm definitely going to do that. Quick question about the name change documentation - I got married last year and changed my name, but I already filed my taxes with my new married name. Do you think I still need to bring my marriage certificate, or would they have that info already since it matches what I filed? Don't want to over-prepare but also don't want to be missing something important!
Ana ErdoΔan
I went through in-person verification about 4 months ago and it was honestly not nearly as intimidating as I thought it would be! Here's what really helped me: I called the IRS office directly the day before my appointment to confirm what documents they needed (sometimes requirements can vary slightly by office), and I'm so glad I did because they mentioned bringing my most recent pay stub which wasn't on the standard list. The actual process was very straightforward - they verify your identity by comparing you to your photo ID, check that your Social Security card is legitimate, and ask a few basic questions about your tax filing. The IRS representative I worked with was actually really friendly and explained each step as we went through it. Total time from check-in to walking out was about 40 minutes, with most of that being wait time. One thing that really put me at ease was that they explain exactly what they're doing and why, so there's no mystery to the process. Just bring all your documents organized in a folder and you'll be absolutely fine! The relief you'll feel walking out knowing it's all taken care of is worth the temporary stress π
Amun-Ra Azra
β’This is so helpful! I love that you called ahead to double-check the requirements - that's such a smart move. The pay stub tip is really valuable too since I wouldn't have thought of that. It's reassuring to hear that they explain each step as they go. I've been overthinking this whole thing but your experience makes it sound much more manageable. Thanks for taking the time to share all these details! π
Rajiv Kumar
One more thing to consider - if you make over a certain amount from your contractor work (I think it's around $1,000), you'll need to file Schedule C along with your tax return. This is where you report business income and expenses. You'll also fill out Schedule SE for self-employment tax. Start keeping track of ALL business-related expenses now if you haven't already! Mileage for business travel (not commuting), home office if applicable, portion of internet/phone, software subscriptions, office supplies, professional development, etc. These can significantly reduce your taxable income.
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Aria Washington
β’Schedule C is super important! And the threshold is actually any net profit, not a specific dollar amount. So even if you only made $500 as a contractor, you still need to file it. The $1,000 threshold is more about when you're required to pay self-employment tax.
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Javier Morales
This thread has been incredibly helpful! As someone who just started contracting this year too, I want to add one thing that caught me off guard - make sure you're tracking your business expenses from DAY ONE, not just when tax season approaches. I learned this the hard way when I realized I had forgotten to save receipts for legitimate business expenses like software subscriptions, equipment purchases, and even parking fees for client meetings. The IRS requires documentation for deductions, so having a system in place early (even something as simple as a dedicated folder or app) can save you hundreds or thousands in missed deductions. Also, don't forget about the home office deduction if you work from home regularly and exclusively use a space for business. You can either use the simplified method ($5 per square foot up to 300 sq ft) or calculate actual expenses. Even if it's just a corner of your bedroom that you use only for work, it might qualify! One last tip: consider making estimated payments for 2025 even if you're not required to. It helps with cash flow management and prevents that massive tax bill shock next April. You can always adjust the amounts throughout the year if your income changes.
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Lydia Santiago
β’Great point about tracking expenses from day one! I wish I had known this when I started. Do you have any recommendations for apps or systems that work well for contractors? I'm currently just throwing receipts in a shoebox which I know isn't sustainable. Also, for the home office deduction - does it matter if you sometimes work from coffee shops or other locations, or can you still claim it as long as you have a dedicated space at home that's your primary work area?
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