This is a really complex situation that I think requires extra caution. While everyone's given great advice about the nominee income approach, I'd strongly recommend getting this documented BEFORE you file your return. The IRS has been cracking down on sports betting income reporting, and having everything properly documented upfront could save you major headaches later. A few additional points to consider: Make sure your friend actually reports the income on their return - if they don't, and the IRS matches your 1099 showing you reported it as nominee income, that could trigger questions for both of you. Also, keep detailed records of the deposit/withdrawal patterns showing the money flow went directly between your friend and the betting site, not through your personal accounts. One more thing - consider whether this arrangement is worth the ongoing tax complexity. Most legitimate sports betting sites have pretty straightforward account creation processes now, so it might be easier for your friend to just set up their own account going forward.

I just want to emphasize something that might get overlooked in all the technical tax advice - make absolutely sure you and your friend are on the same page about reporting this correctly. I've seen situations where one person files using the nominee income approach, but then the actual recipient doesn't report it on their return (either by mistake or thinking they don't need to since someone else already "claimed" it). This creates a huge red flag for the IRS because they'll see gambling winnings reported under your SSN with an offsetting deduction, but no corresponding income reported by your friend. That's almost guaranteed to trigger correspondence or an audit for both of you. I'd suggest you both file at the same time if possible, or at least coordinate so you know your friend has actually included the $9,200 as gambling income on their return before you submit yours. Also keep copies of both returns for your records - if questions come up later, being able to show that both parties properly reported their respective sides of the transaction will go a long way toward resolving any IRS inquiries quickly.

Great to see this resolved! For future reference, you can also contact your brokerage directly if you can't find the tax documents online - they're required to provide you with the dividend information even if they don't send a formal 1099-DIV for amounts under $10. Most brokerages have a dedicated tax support line during filing season that can quickly provide you with the details you need. This can be especially helpful if you have multiple small dividend payments from different stocks and want to make sure you're capturing everything accurately.

As someone who works in tax preparation, I just wanted to emphasize a few key points from this discussion for anyone else in a similar situation: 1. **Always report ALL dividend income** - regardless of amount or whether you received a 1099-DIV 2. **Check your brokerage account online** - most have tax documents available even for small amounts 3. **Qualified vs. ordinary dividends matter** - qualified dividends get better tax treatment, so it's worth checking 4. **Keep good records** - save screenshots or downloads of your brokerage tax summaries for your files The IRS has sophisticated matching systems that can catch unreported income even for small amounts. While $14 won't break the bank in taxes owed, getting into good compliance habits early will serve you well as your investment portfolio grows. Plus, it's honestly not that difficult once you know the process - probably took you longer to write this post than it would to actually report the dividends!

I'm going through this exact same nightmare right now! My business partner and I made the identical mistake when applying for our EIN - checked "corporation" instead of "LLC with partnership taxation." We've been spinning our wheels for months trying to get this fixed. Reading through everyone's experiences here has been incredibly reassuring. It sounds like Form 8832 is definitely the way to go, and I'm relieved to learn that 7 months is well within the timeframe for retroactive relief under Rev. Proc. 2009-41. I especially appreciate the detailed breakdown of supporting documents to include - our operating agreement explicitly states partnership taxation from day one, so that should help strengthen our case. The certified mail tip is also something I hadn't thought of but makes total sense for creating a paper trail. One question for those who've been through this process: did any of you have to deal with your bank or other financial institutions during the classification correction? I'm wondering if having the wrong entity type on file with our business bank account could cause any complications while we're waiting for the Form 8832 to be processed. Thanks to everyone for sharing their experiences - it's giving me confidence that we can actually get this resolved without having to start over with a new EIN like that third IRS rep suggested!

I'm dealing with this exact same issue right now! My partner and I accidentally selected "corporation" instead of "partnership" when we applied for our EIN last year, and we only discovered the mistake when our accountant started preparing our first tax return. After reading through all these detailed responses, I feel much more confident about the path forward. The Form 8832 approach with retroactive relief under Rev. Proc. 2009-41 seems to be the consistent recommendation from everyone who's successfully navigated this process. What really stands out to me is how many people got conflicting advice from different IRS representatives - it's frustrating but apparently very common. The detailed breakdown of supporting documents to include (state LLC formation docs, operating agreement, CP 575 notice, reasonable cause statement) is incredibly helpful. I'm particularly grateful for the tips about certified mail and the realistic timeline expectations (6-8 weeks for processing). After months of uncertainty, it's reassuring to know there's a clear, proven path to get this corrected without having to start over with a new EIN. For anyone else in this situation - don't give up! It seems like this mistake is more common than we think, and the IRS has established procedures to fix it. The key is being thorough with your Form 8832 submission and including all the necessary supporting documentation upfront.

This has been an absolutely fantastic discussion to read through! As someone who just joined this community and is new to HSA regulations, I'm amazed by the depth of real-world experience shared here. What I find most valuable is how this thread demonstrates the importance of community knowledge in navigating complex tax situations. The official IRS guidance on HSA eligibility can be pretty vague, but hearing from people who've actually been through audits, worked with tax professionals, and successfully structured their concierge agreements provides the practical clarity we all need. A few key takeaways I'm noting for future reference: 1. **Contract language is critical** - The difference between "membership fee" and "prepayment for medical services" could determine HSA eligibility 2. **Documentation matters** - Keep detailed records of services actually received, not just what's available 3. **Provider credentials count** - Licensed MDs/DOs are safer than alternative practitioners for HSA purposes 4. **Professional guidance helps** - Whether through tax preparers, specialized tools, or IRS consultation services For anyone else new to this topic, this thread is a perfect example of why community forums like this are so valuable. You get practical, tested advice that goes way beyond what you'll find in official publications. Thanks to everyone who shared their experiences - this kind of knowledge sharing makes navigating government services so much more manageable!

As someone who's been researching this exact question for weeks, this thread has been incredibly enlightening! I'm new to this community but have been struggling with the same HSA eligibility concerns about my concierge medicine fees. What really stands out to me is how much the actual contract language matters. I had no idea that the difference between calling it a "membership fee" versus "prepayment for medical services" could be so significant for HSA purposes. I'm particularly grateful for @Genevieve Cavalier sharing the real audit experience - that's exactly the kind of validation we need to understand how the IRS actually interprets these rules in practice. And the professional insights from tax preparers like @Paolo Longo about specific documentation requirements are invaluable. Based on everything shared here, I'm going to approach my concierge practice about revising our agreement to explicitly itemize the medical services covered by my monthly fee. It sounds like many practices are familiar with this issue and have HSA-friendly contract versions available. This discussion has provided more practical guidance than months of trying to decipher IRS publications on my own. Thank you to everyone who shared their real-world experiences - this is exactly why community forums are so valuable for navigating complex government regulations!

Great thread! Just to add one more resource - if you're still feeling uncertain about the filing requirements after using tax software, the IRS has a really helpful Interactive Tax Assistant tool on their website (irs.gov/help/ita). You can walk through a series of questions about your daughter's specific situation and it will give you a definitive answer about whether filing is required. I used it last year when my nephew had a similar situation with both W-2 income and investment sales. The tool is free, official, and takes into account all the different thresholds and rules that apply to dependents. It's particularly useful because it considers the interaction between earned income, unearned income, and gross proceeds from sales. Since you mentioned this is her first year investing, you might also want to keep good records of all her transactions beyond just what's on the 1099-B. If she continues investing, having detailed records of purchase dates, amounts, and any reinvested dividends will be invaluable for future tax years. Good luck with the filing!

This is such a valuable discussion! I'm dealing with a similar situation with my 16-year-old who started investing with birthday money. One thing I learned the hard way is that even though the gross proceeds threshold triggers the filing requirement, you also need to be careful about how the cost basis is reported on the 1099-B. Some brokerages don't track cost basis for stocks purchased before certain dates, or they might not have complete information if the stocks were transferred from another account. If the cost basis shows as "not reported to IRS" or is blank on the 1099-B, you'll need to provide that information on the tax return yourself. I'd recommend double-checking that the $2,800 cost basis on your daughter's 1099-B matches your records of what was actually paid for the stocks. If there are any discrepancies, you'll want to have documentation ready to support the correct cost basis when filing. The IRS will definitely notice if the reported gain doesn't match what they expect based on the 1099-B information they receive.