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Ask the community...

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Chloe Harris

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Just wanted to suggest filing Form 8275 (Disclosure Statement) with the IRS when you deal with this. I had a similar issue with a different tax prep company and this form helped document that the filing delay wasn't my fault but was due to preparer error. Attach it to your response to the IRS when requesting penalty abatement.

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Form 8275 is generally for disclosing positions taken on your return that might be challenged, not for explaining late filing due to preparer error. For penalty abatement, you'd typically write a letter explaining the situation or call the IRS directly. Just want to make sure OP has accurate info.

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Zara Shah

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I went through almost the exact same situation with Jackson Hewitt two years ago - they failed to file my return on time despite me submitting everything weeks before the deadline. The key is being persistent and escalating properly. First, absolutely contact the regional manager you got info for. When you do, reference their "Maximum Refund Guarantee" terms specifically - most people don't realize this also covers penalties from their filing errors, not just audit protection. I found a copy of my guarantee paperwork that explicitly stated they'd cover "penalties resulting from preparer error in filing." Second, if the regional manager doesn't resolve it immediately, escalate to Jackson Hewitt's corporate complaint department. I had to threaten to file complaints with both the Better Business Bureau and my state's Department of Consumer Affairs before they took it seriously. The breakthrough for me was when I pointed out that failing to honor their guarantee could be considered deceptive business practices under consumer protection laws. Within a week of mentioning potential regulatory complaints, they cut me a check for the full penalty amount. Don't give up - you paid extra for that protection specifically for this scenario. Document every conversation with names, dates, and reference numbers. They're banking on you getting frustrated and paying out of pocket, but you have a legitimate contractual claim here.

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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!

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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.

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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.

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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.

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Zara Malik

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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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What about cash expenses for business? I sometimes pay day laborers in cash for help with my landscaping business - how do I prove these are legitimate?

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For cash payments, you need to create your own receipt system. I have a receipt book where I write the person's name, date, amount paid, and what work they did. Then have them sign it. I also track ATM withdrawals that match these payments. It's not perfect but it creates a paper trail.

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Great thread! As someone who went through my first business tax filing this year, I learned the hard way that organization is EVERYTHING. The IRS basically expects you to be able to prove every single deduction you claim. One thing that really helped me was setting up a simple system from day one: I use a dedicated business checking account, immediately photograph receipts with my phone, and keep a simple spreadsheet noting the business purpose of each expense. Even small purchases like office supplies get documented. The key insight I had is that the IRS isn't necessarily looking to catch you doing something wrong - they just want to see that you're being reasonable and keeping proper records. If you can show clear business purpose and have documentation to back it up, you're usually fine. For anyone just starting out like the original poster, my advice is to err on the side of over-documenting rather than under-documenting. It's way easier to establish good habits from the beginning than to try to reconstruct everything later if you get audited.

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This is exactly the kind of advice I needed to hear! I'm also in my first year of business tax filing and feeling overwhelmed by all the documentation requirements. Your point about over-documenting really resonates - I've been worried about going overboard with record keeping, but it sounds like that's actually the safer approach. Quick question: for the spreadsheet you mentioned, do you track anything beyond just the business purpose? Like do you note the category of expense (office supplies, travel, etc.) or is that overkill?

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I've been through this exact same situation and completely understand that initial panic! 😰 The good news is that this is incredibly common and the IRS has streamlined processes to handle it. Here's my personal experience: I forgot my 1095-A in 2023, realized it after my return was accepted, and initially thought I was in big trouble. Turns out I actually got an additional $750 refund when I amended because my actual income ended up being lower than what I estimated for marketplace coverage! **Quick checklist that saved me stress:** - First, check boxes 21-23 on your 1095-A (advance premium tax credits received) - If blank/$0, you likely don't need to amend at all - If there are amounts, file 1040-X with Form 8962 when your original return finishes processing **Timeline reassurance:** Your original refund will come through completely normal - mine arrived right on schedule while the amendment processed separately. So your spring home repair timeline should be perfect! šŸ  The amendment took about 9 weeks to process when I e-filed it, which is way faster than the old paper system. Don't beat yourself up about this - you're being proactive and that's exactly the right approach. Based on all the experiences shared here, you'll likely come out ahead financially! You've got this! šŸ’Ŗ

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Ella Harper

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I went through this exact situation last year and can totally relate to that panic feeling! šŸ˜… Here's what I learned: **First check your 1095-A boxes 21-23** - if they show $0 or are blank, you likely don't need to amend since you didn't receive advance premium tax credits (APTC). If there ARE amounts there, then yes, you'll need Form 1040-X with Form 8962. **The encouraging part:** I actually ended up with an additional $580 refund! My actual income was lower than my marketplace estimate, so I was entitled to more premium tax credits than I originally received. **Your timeline concerns:** Your original refund processes completely separately and won't be delayed. Mine came through right on schedule in February while my amendment was still being processed. Got the additional refund in May after e-filing the amendment. For your spring home repairs - you should be totally on track! The original refund timeline stays the same regardless of whether you need to amend. And if you do amend, any additional money would just be bonus renovation funds! šŸ  Don't stress too much about this - it's way more common than you think, and the IRS process is pretty straightforward. E-filing amendments now only takes about 8-10 weeks versus the old 16+ week paper processing times. You caught this early and you're handling it proactively - that's exactly the right approach! šŸ’Ŗ

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Anyone know if these ticket sales count toward the threshold where you need to make estimated tax payments? I normally just get a W-2 but sold about $8k in tickets last year and made like $1500 profit.

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Yes - ANY income, including ticket sales, counts toward whether you need to make estimated tax payments. The rule is you need to pay 90% of your tax liability during the year OR 100% of last year's tax liability (110% if your AGI was over $150k).

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Lydia Bailey

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For anyone still confused about this, I just want to clarify the key points since there's some conflicting advice in this thread: 1. You MUST report the full 1099-K amount as gross income - don't just report the net profit like one commenter suggested. The IRS computer systems automatically match 1099-K forms to tax returns, and reporting only the net will trigger a notice. 2. Whether you use Schedule C or Schedule 1 depends on your intent and frequency. If you bought tickets specifically to resell for profit or do this regularly, it's a business (Schedule C). If you're just selling tickets you can't use occasionally, it's hobby income (Schedule 1, Line 8i). 3. You can deduct BOTH your original ticket costs AND the platform fees. The 1099-K shows gross payments before StubHub's fees were deducted, so you're not double-counting anything. 4. Keep good records! Save your original purchase confirmations, credit card statements, and any communications about the sales. The IRS may ask for documentation. The software tools mentioned here (taxr.ai) seem helpful for organizing everything, but make sure you understand the fundamentals so you can verify the results make sense.

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Zoe Wang

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Thank you so much for this clear breakdown! This is exactly what I needed to hear. I was getting really confused by all the different advice, especially about whether to report gross vs net. One follow-up question - you mentioned keeping records of communications about the sales. What kind of communications are important? I have my StubHub sale confirmations and the original ticket purchase emails, but is there anything else I should be documenting for potential IRS questions? Also, since this was truly a one-time thing for me (sold tickets to a concert I couldn't attend anymore), I'm assuming Schedule 1 is the right approach rather than Schedule C?

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