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Has anyone here used TurboTax for reporting crypto gambling? Their help section is useless and I can't figure out how to properly categorize my crypto gambling gains.
I tried using TurboTax for my crypto last year and it was a disaster for anything beyond basic buying/selling. Had to switch to a dedicated crypto tax software halfway through. For gambling specifically, they have you report winnings under "Other Income" on Schedule 1, but they don't handle the crypto withdrawal part well at all.
Thanks for the response. That's what I was afraid of. Did you end up using a different tax software altogether or did you just supplement TurboTax with something else for the crypto part?
I actually dealt with a very similar situation last year. The key thing to understand is that you're dealing with two separate tax events here: (1) gambling income when you win, and (2) crypto capital gains/losses when the ETH value changes after you receive it. For the gambling side, report your net winnings as "Other Income" on your tax return. For the crypto side, when you withdrew ETH from the gambling site, that ETH has a cost basis equal to its fair market value at the exact moment you received it in your wallet. If the ETH dropped in value after that, the $101 capital loss your software is showing is legitimate and should be reported on Schedule D. Make sure you have documentation of when exactly you received the ETH withdrawal - the timestamp and market value at that moment establishes your cost basis. Most people miss this step and it can cause issues later if you're audited. The important thing is not to double-count anything. Don't report the same money as both gambling income AND crypto income. Keep the two activities separate in your records and reporting.
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Some companies are just terrible about getting 1099s out on time. Last year I had a client who didn't send mine until March despite multiple reminders! What I ended up doing was creating a really detailed spreadsheet of all the invoices and payments, then filed with that info. The 1099 finally showed up later and the numbers matched my records exactly. If you know how much you earned from them, you can still file your taxes without waiting. As long as you report the income accurately, you're meeting your obligation. The 1099 is more about the IRS tracking that companies are properly reporting payments than it is about you proving your income.
That makes sense, but wouldn't you need the 1099 to have their tax ID number? Or is that not really necessary when you're filing?
Great question! You actually don't need their tax ID number to report self-employment income on your Schedule C. You'll list your income in total rather than breaking it down by each payer. The tax ID number is more important for the company issuing the 1099 for their reporting requirements. If you're dealing with 1099-MISC or 1099-NEC forms, you'd typically just report the total income on your Schedule C without needing to list each company's ID. Now, if you're dealing with other types of 1099s like interest or dividends, those might require more specific reporting. But for standard freelance/contractor work, you're good to go with just accurately reporting the amount you earned.
This happened to me last year with a new client! The company was a startup and their finance person had no idea about the January 31 deadline 🤦♀️ I ended up filing Form 4852 (substitute for missing W-2/1099) with my tax return. You basically create your own substitute based on your records.
Is there any downside to filing that substitute form? Like does it trigger an audit or anything?
From my experience, filing Form 4852 doesn't automatically trigger an audit. The IRS actually expects people to use this form when they can't get the proper documents from their employers or clients. The key is making sure your substitute form is as accurate as possible based on your own records. I kept detailed records of all my invoices and payments, so when I filed the substitute, the numbers were spot-on. When the actual 1099 finally arrived a few weeks later, it matched perfectly. The IRS is more concerned with people who don't report income at all rather than those who are making a good faith effort to report everything accurately, even without the official forms. Just make sure you attach a statement explaining why you're using the substitute form (like "1099 not received despite multiple requests").
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As a tax professional who has helped numerous clients implement self-rental arrangements, I want to emphasize something that hasn't been fully addressed yet: the importance of getting this right from the very beginning. I've seen too many taxpayers try to retroactively create documentation after receiving IRS notices, which rarely ends well. The IRS is particularly sophisticated in detecting arrangements that appear to have been constructed primarily for tax avoidance rather than legitimate business purposes. Here's what I recommend for anyone considering this strategy: **Before you start**: Have a tax professional model out your entire tax situation over multiple years. Sometimes the SE tax savings are offset by other factors (like losing certain deductions or credits), and you want to understand the complete picture. **Documentation timeline**: Start documenting your business justification and market research at least 30 days before your lease begins. This shows advance planning rather than reactive tax planning. **Professional oversight**: Don't try to navigate this alone. The regulations around self-rental (particularly IRC Section 469 and the related regulations) are complex, and small mistakes can be costly. The passive/non-passive income classification that several people mentioned can be a double-edged sword - while it might help with suspended losses, it can also affect your ability to claim certain passive activity deductions in future years. One final note: make sure you're also considering the depreciation recapture implications if you ever sell the property. Converting personal residence depreciation to business property depreciation changes your tax obligations upon sale.
This is incredibly valuable professional insight! As someone who has been lurking and learning from this entire discussion, your point about getting everything right from the beginning really hits home. I was actually about to rush into setting up a self-rental arrangement after reading all the positive experiences shared here, but your warning about retroactive documentation is making me pump the brakes. The 30-day advance documentation timeline you mentioned is particularly helpful - I hadn't realized that the timing of when you create your business justification documentation could be scrutinized by the IRS. It makes complete sense that they would view advance planning more favorably than reactive documentation. Your point about modeling the complete tax picture over multiple years is something I definitely need to do. I've been so focused on the immediate SE tax savings that I hadn't fully considered how this might affect my overall tax strategy in future years, especially the depreciation recapture implications you mentioned. One question: when you say "have a tax professional model out your entire tax situation," are there specific scenarios or variables you typically run through with clients? I want to make sure I'm asking the right questions when I meet with a CPA about this. Also, regarding the IRC Section 469 regulations you referenced - are there any particular aspects of these regulations that trip up taxpayers most frequently? I'd rather know about potential pitfalls upfront rather than discover them during an audit. Thank you for sharing your professional perspective - it's exactly the kind of guidance that helps ensure this strategy is implemented properly rather than creating future problems!
When I model scenarios for clients, I typically run projections for at least 3-5 years looking at: current year SE tax savings, impact on QBI deduction eligibility, changes to passive activity loss utilization, potential AMT implications, and future depreciation recapture upon property sale. I also model what happens if rental rates change significantly or if their business income fluctuates. Regarding IRC Section 469, the most common pitfalls I see are: 1) Misunderstanding the material participation rules and how they affect the passive/non-passive classification, 2) Not properly tracking basis adjustments when depreciation is involved, and 3) Failing to understand how the self-rental rules interact with other passive investments they may have. The regulations are particularly tricky around the "significant participation" and "material participation" tests. Many taxpayers assume that since they own both the business and the property, the rental income is automatically non-passive, but the actual determination can be more complex depending on their level of involvement in the rental activity itself. I always recommend clients work with a CPA who regularly handles these arrangements rather than trying to navigate the regulations independently. The upfront cost of professional guidance is minimal compared to the potential costs of getting it wrong and facing IRS adjustments, penalties, and interest later.
This entire discussion has been incredibly enlightening! As someone who's been running a small marketing consultancy from my home office for the past year, I've been leaving money on the table by not exploring the self-rental arrangement. What strikes me most from reading everyone's experiences is how critical proper documentation and professional guidance are. The difference between a successful arrangement and one that gets challenged by the IRS seems to come down to treating this as a legitimate business transaction from day one, not just a tax strategy. I'm particularly interested in the point @Anastasia Sokolov made about modeling the complete tax picture over multiple years. It sounds like the SE tax savings are just one piece of a more complex puzzle that includes QBI deduction impacts, passive loss utilization, and future depreciation recapture considerations. The practical tips shared here about separate bank accounts, quarterly market rate analyses, and formal lease renewals give me a clear roadmap for implementation. I also appreciate the warnings about consistency - this needs to be a long-term business strategy, not something you start and stop based on annual income fluctuations. My next steps are to document my business justification for needing dedicated office space, get a professional market rent analysis, and find a CPA experienced with these arrangements to model out the multi-year tax implications. The upfront investment in professional guidance seems minimal compared to the potential risks of getting this wrong. Thanks to everyone who shared their real-world experiences and professional insights - this has been one of the most valuable tax discussions I've encountered!
This has been such a comprehensive discussion! As someone just discovering this community, I'm amazed by the depth of practical experience everyone has shared about self-rental arrangements. What really stands out to me is how this strategy requires treating it like a genuine business relationship rather than just a tax maneuver. The emphasis on documentation, market-rate rent, and consistent business practices makes complete sense from an IRS perspective. I'm particularly intrigued by the multi-year modeling approach that @Anastasia Sokolov mentioned. It sounds like the immediate SE tax savings might just be the tip of the iceberg when you factor in QBI deductions, passive loss utilization, and depreciation considerations. This is definitely more complex than I initially realized. The timing aspect is also crucial - starting documentation 30 days before implementation and maintaining consistency across years shows this needs to be a thoughtful, long-term business decision. I appreciate everyone being so transparent about both the benefits and the compliance requirements. For anyone else considering this strategy, it seems like the key takeaway is: invest in proper professional guidance upfront, document everything thoroughly, and treat it like the legitimate business arrangement it needs to be. The potential tax savings sound significant, but only if implemented correctly from the start.
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This thread has been incredibly helpful! I'm in a similar situation as the original poster - just got accepted into TikTok's creator program from Canada and was completely overwhelmed by the TIN requirement. Reading through everyone's experiences, it sounds like the ITIN application process is much more manageable than I initially thought. The key takeaways I'm getting are: 1. **Use Form W-7 with Exception 1(d)** for third-party withholding 2. **Find a local Certifying Acceptance Agent** to avoid mailing original documents 3. **Be specific about the purpose** - mention "third-party information reporting for social media monetization" 4. **Keep all TikTok communications** as proof of business need 5. **Expect 7-11 weeks processing time** but TikTok is understanding about delays For other Canadians reading this, I'm going to start researching CAAs in Toronto/Vancouver. The £150-200 fee mentioned by UK folks seems totally reasonable to avoid the stress of international document mailing. One question for those who've completed the process - did you have any issues with your home country's tax authority? I want to make sure filing US returns won't complicate things with CRA, especially regarding the tax treaty benefits everyone's mentioned. Thanks again to everyone who shared their experiences - this community is amazing!
Hey! Fellow Canadian here who went through this exact process about 6 months ago. You're absolutely right that it's much more manageable than it initially seems - the community advice in this thread is spot on! For Canada specifically, I found a great CAA in Toronto called Cross-Border Tax Solutions. They handle a lot of creator/influencer cases and were really familiar with the TikTok requirements. Cost was around $225 CAD but totally worth avoiding the passport mailing stress. Regarding CRA concerns - you shouldn't have any issues! The US-Canada tax treaty prevents double taxation, so you'll claim a foreign tax credit on your Canadian return for any US taxes withheld. Most of the time, your effective US tax rate will be lower than Canadian rates anyway, so you might not even owe additional Canadian tax on the TikTok income. Just make sure to keep good records of any US taxes paid. The key is properly completing the W-8BEN form for TikTok to claim treaty benefits upfront - this reduces US withholding from 30% to around 10% for most types of creator income. Way better to get it right from the start than try to recover over-withheld taxes later! Feel free to reach out if you have other Canada-specific questions - happy to help a fellow creator navigate this maze!
This thread has been such a lifesaver! I'm actually in a slightly different situation - I'm a US citizen living abroad (Japan) who got accepted into TikTok's creator program, and I was confused about whether I needed to do anything special for the TIN requirement since I already have a Social Security Number. After reading through all these experiences with ITINs, I realize I probably just need to provide my SSN and fill out a W-9 form since I'm still a US person for tax purposes. But now I'm wondering about the tax implications of earning TikTok income while living overseas - do I need to worry about Japanese taxes on this income too? Has anyone dealt with being a US citizen abroad in creator programs? I'm worried about getting hit with taxes in both countries, especially since Japan has pretty high tax rates. The foreign earned income exclusion probably doesn't apply to social media income, right? Would love any insights from other expat creators or anyone who understands the cross-border tax situation!
Elijah Knight
My company did the same thing! No code DD on my W-2 this year. I called HR and they didn't even know what I was talking about 🤦♀️ When I explained it was the health insurance cost reporting, they just said "we follow all IRS requirements" and brushed me off. Really frustrating when you're trying to understand your own compensation.
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Brooklyn Foley
•Same experience here. HR departments seem completely clueless about tax forms sometimes. I ended up finding my health insurance cost by looking at my benefits enrollment confirmation email from last year. It showed both my contribution and the company portion, which would have been the Code DD amount. Worth checking if you kept those emails!
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Mae Bennett
This is a really common issue that I've seen come up a lot lately. The code DD reporting requirement is still active under the ACA, but as others mentioned, it only applies to employers who issued 250 or more W-2s in the previous tax year. One thing to keep in mind is that if your employer changed payroll providers or went through a merger/acquisition, this could affect how they count towards that 250 threshold. Also, some employers mistakenly think this reporting is optional because there aren't heavy penalties specifically for missing code DD. If you want to find out your actual health insurance costs, you can also check your Summary Plan Description (SPD) or Annual Notice that your employer is required to provide. These documents usually break down the total premium costs. Your employee benefits portal might also have this information under plan details or cost summaries.
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Connor Gallagher
•This is really helpful information! I hadn't thought about checking the Summary Plan Description - I probably have that buried in my email somewhere from open enrollment. One question about the merger/acquisition scenario you mentioned - if my company was acquired by a larger company last year, would that change the 250 employee threshold calculation? Like, would they count the combined employee base or just our original company's size for determining the reporting requirement? Also, do you know if there's a specific deadline by which employers have to provide those Annual Notices? I don't remember getting one recently but maybe I overlooked it.
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