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Has anyone tried reporting this kind of thing using TurboTax or H&R Block software? I'm in a similar situation and wondering which tax software handles gambling income/losses through proxy betting the best.
I used TurboTax last year for a similar situation. It handles the gambling income/loss reporting fine, but doesn't really guide you through the documentation aspect which is what really matters. You'll need to organize all that yourself regardless of what software you use.
I went through something very similar last year and can share what worked for me. The key thing to understand is that the IRS focuses on economic substance - who actually owned the money and bore the risk of the bets. Here's what I did that helped: 1. Created a detailed log showing every transfer to friends with dates, amounts, and purposes 2. Screenshots of all text conversations coordinating bets 3. Bank/payment app statements showing the money flow 4. Written statements from my friends confirming they were placing bets on my behalf with my money For the W-2G issue, my friend and I worked with a CPA to handle it properly. My friend reported the W-2G income on his return, then we documented the transfer to me as the beneficial owner. I reported the same amount as gambling income on my return with supporting documentation. The most important thing is having a clear paper trail. The IRS auditor I eventually spoke with said they see this situation more often than you'd think, and as long as you can prove the money was yours and you're honestly reporting everything, they're not concerned with platform terms of service violations. One tip: calculate whether itemizing actually saves you money before going that route. In my case, I had enough other deductions to make itemizing worthwhile, but if gambling losses are your only major deduction, the standard deduction might be better financially.
This is really helpful, thank you! I'm curious about the timeline - how long did it take from when you filed your return to when you actually spoke with an IRS auditor? I'm trying to prepare myself mentally for how long this process might drag out. Also, did having the written statements from your friends make a big difference, or was the electronic transfer documentation sufficient on its own?
Has anyone just manually entered their crypto transactions into TurboTax? I only have about 40 trades for the year so wondering if that's easier than dealing with all these third-party services.
I tried that one year when I had about 30 transactions. It was tedious but doable. Just make sure you have all the correct dates, amounts, and cost basis for each transaction. The problem comes when you have crypto moving between different exchanges or wallets, as it gets really complicated to track the cost basis manually.
Thanks for the input. Maybe I'll try the manual approach since my situation isn't too complex. Just wanted to make sure I wasn't making things harder than they need to be!
I've been dealing with this exact same issue! What worked for me was using FreeTaxUSA instead of TurboTax - it has better support for importing crypto transactions directly from CSV files. I was able to upload my crypto.com transaction history with minimal formatting issues. If you're set on using TurboTax though, I found that cleaning up the crypto.com CSV file first made a huge difference. Remove any duplicate entries, make sure all dates are in MM/DD/YYYY format, and verify that buy/sell amounts match up properly. Sometimes crypto.com includes partial fills as separate transactions which can mess up the import. For the cost basis calculation differences between platforms, double-check how they're handling your staking rewards and any crypto-to-crypto trades. Those are usually where the biggest discrepancies come from.
That's a great point about FreeTaxUSA! I hadn't considered switching tax software entirely. Quick question - does FreeTaxUSA handle all the same deductions and credits as TurboTax? I've been using TurboTax for years mainly because I have some rental property income and wasn't sure if other platforms would be as comprehensive. Also, when you say "cleaning up the CSV file" - do you have any specific recommendations for tools or methods? I'm not super technical but can handle basic spreadsheet editing if needed.
Has anyone dealt with property taxes paid to foreign governments? Can those be deducted on US taxes? I'm in a similar situation with my parents buying in Ecuador.
Foreign property taxes CAN be deducted, but only if they're based on the assessed value of the property (similar to how US property taxes work). If they're flat fees or service charges, they wouldn't qualify. Also, remember your parents need to itemize deductions to claim this - it doesn't work with the standard deduction.
This is such a complex situation! Your parents definitely need to be prepared for ongoing US tax obligations. One thing I haven't seen mentioned yet is the potential impact on their state tax situation. Depending on which state they currently live in, they may need to officially establish tax residency elsewhere before moving to avoid continued state tax obligations. Also, since they're planning to split time between countries, they should be very careful about the substantial presence test. Even though they're US citizens (so it doesn't affect their filing requirement), it could impact how certain deductions and credits are calculated. I'd strongly recommend they consult with a tax professional who specializes in expat taxes BEFORE making the purchase. The timing of when they buy, when they move, and how they structure their finances could significantly impact their tax burden. Getting advice upfront could save them thousands in taxes and penalties down the road.
I'm confused about withholding in these multi-state situations. My company withholds for my resident state (Oregon), but I travel to Washington and California for work regularly. Should I be having them withhold for those states too? Or do I just figure it out at tax time?
You should definitely set up withholding for states where you work regularly, especially California which is notorious for going after non-resident income. Otherwise you might face underpayment penalties. Your payroll department should be able to set up multiple state withholdings based on the approximate days you'll work in each location.
Great thread! I'm dealing with a similar situation but with a twist - I'm a freelancer with clients in multiple states. I have clients in Texas (no income tax), New York, and California, and I live in Colorado. From what I've learned, freelancers face even more complexity because we don't have employers handling withholdings. Each state has different rules about when freelance income is considered "sourced" to their state - some base it on where the work is performed, others on where the client is located, and some on where the services are delivered. For example, if I do graphic design work from my home office in Colorado for a New York client, some states would consider that Colorado income, while others might try to claim it as New York income if that's where the "benefit" of my work is received. Has anyone dealt with freelance income across state lines? I'm trying to figure out if I need to file non-resident returns in every state where I have clients, or if Colorado covers it all since I physically perform the work here.
Effie Alexander
Can anyone confirm if we're supposed to check box 13b on Schedule A of Form 8936? The instructions are unclear but that box specifically asks if you transferred the credit to the dealer.
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Melissa Lin
ā¢Yes, absolutely check box 13b! That's the flag that tells the IRS system you transferred the credit. Then enter $0 on Schedule 3. I spoke with my uncle who works at the IRS (in a different department but still familiar with these forms) and he confirmed this is the correct procedure.
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AstroAdventurer
Thanks everyone for the detailed responses! This has been incredibly helpful. I was definitely overthinking this situation. Based on what I'm reading here, it sounds like the consensus is: 1. Complete Form 8936 showing I qualify for the credit 2. Check box 13b on Schedule A indicating I transferred to dealer 3. Enter $0 on Schedule 3 Line 6f with "TRANSFERRED" notation 4. Attach a statement referencing IRC Section 30D(g) with my dealer documentation I really appreciate the specific IRC section references and sample statement language from @Hugh Intensity - that gives me confidence I'm documenting this properly. And @Melissa Lin, thanks for confirming about box 13b, I was definitely unsure about that checkbox. It's frustrating that the IRS instructions don't make this clearer, but at least there seems to be a consistent approach that works. I'll go with this method and keep all my documentation organized in case there are any follow-up questions. You've all saved me from either underpaying my taxes or spending hours on hold trying to reach the IRS directly!
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Juan Moreno
ā¢This is such a great summary of all the advice in this thread! I'm dealing with the same exact situation and was getting overwhelmed by all the conflicting information I found online. Having it broken down into those clear steps makes it much more manageable. One quick question - when you attach the statement, are you including it as a separate page or writing it directly on the form somewhere? I want to make sure the IRS processors see it and don't miss the explanation for why I'm showing $0 on Schedule 3 despite qualifying for the credit. Also really appreciate everyone sharing their experiences here. It's reassuring to know this is a common issue and there's a established way to handle it properly.
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