Does anyone know if FreeTaxUSA handles the new digital nomad visa situations? I split 2022 between Colombia, Portugal, and Mexico on various remote work visas while working for a US company that paid me as a contractor (1099-NEC). So technically it's US income but earned while I was physically abroad. I'm so confused about where to put this!

Just wanted to add something that helped me when I was in a similar situation. If you're using FreeTaxUSA and dealing with foreign income, make sure you also check if you need to file Form 8938 (FATCA) in addition to the FBAR that Lucy mentioned. The thresholds are different - FBAR is required if your foreign accounts exceeded $10,000 at any point during the year, but Form 8938 has higher thresholds (generally $50,000 for single filers living in the US, or $200,000 if you're living abroad). However, both forms cover foreign financial accounts and the penalties for not filing can be severe. FreeTaxUSA doesn't handle FBAR (that has to be filed separately through FinCEN), but it does include Form 8938 if you need it. Just something to keep in mind as you're working through your foreign income reporting!

I had this exact same situation with Vivid Seats earlier this year! Initially I was super suspicious too, but after doing some research I found out it's completely legitimate. The SSN request is actually required by federal tax law - payment platforms have to collect this info for anyone they pay, regardless of the amount. The good news is that since you sold at a loss, you won't actually owe taxes on this. You'll report it as a capital loss on Schedule D when you file - $330 cost basis minus $120 proceeds equals a $210 loss that could even help offset other gains you might have. My advice: just give them your SSN and take the $120. Keep your original purchase receipt though - that's your proof of what you originally paid. Even if you get a 1099-K showing the $120 payment, your receipt will prove to the IRS this was actually a loss, not taxable income. It's annoying to deal with extra paperwork when you're already getting ripped off, but $120 is definitely better than nothing!

I totally get your frustration - this happened to me with StubHub last year and I was convinced it was some kind of scam at first! But after going through it myself, I can confirm that the SSN request is completely legitimate. Payment platforms are required by federal law to collect this information for tax reporting purposes. The silver lining is that since you're selling at a significant loss ($330 original cost vs $120 sale), you definitely won't owe any taxes on this transaction. In fact, you'll have a $210 capital loss that you can report on Schedule D, which might actually help reduce your tax burden if you have other capital gains. My recommendation is to go ahead and provide your SSN to get your $120. Just make absolutely sure to keep your original Ticketmaster purchase receipt - that's going to be your proof of the $330 cost basis if you ever need to document the loss. Even if you receive a 1099-K showing $120 as income, your receipt will prove this was actually a loss once you account for what you originally paid. It's definitely annoying to deal with extra tax paperwork when you're already getting screwed by their resale prices, but $120 is still better than forfeiting it entirely. The tax reporting requirements aren't Ticketmaster's fault in this case - they're just following IRS regulations that now apply to all payment platforms.

As a newcomer to independent contractor taxes, this thread has been incredibly helpful! I'm in a similar situation doing part-time delivery work and had no idea about the distinction between regular meals (not deductible) vs. travel meals when you're away from your normal business area. One thing I'm still confused about - how do you define your "tax home" or "normal business area" when you're doing deliveries? Is it based on where you live, or the area you typically cover for deliveries? I usually work within about a 30-mile radius of my house, but occasionally get those longer rural routes that take me 50+ miles out. Would love to understand better when those longer trips might qualify for the meal deduction rules that were mentioned. Also really appreciate everyone sharing the different tools and resources - definitely going to look into better mileage tracking since that seems like the bigger opportunity here!

Just wanted to add another perspective as someone who's been doing independent contractor work for several years. One thing that helped me tremendously was setting up a separate business checking account and business credit card specifically for all my contractor expenses. This makes tracking everything so much cleaner come tax time. For meals specifically, I learned the hard way that the IRS is pretty strict about the business purpose requirement. I used to think any meal while "on the job" counted, but after getting some guidance from a tax pro, I realized most of my regular delivery route meals were just personal expenses that happened to occur during work hours. The real game-changer for me was focusing on the bigger deductions like mileage, phone expenses (you can deduct the business portion), and equipment costs. I also deduct things like insulated delivery bags, phone mounts, and even a portion of my car insurance since I use my vehicle for business. Keep detailed records of everything though - date, amount, business purpose. The IRS loves documentation if they ever come knocking. Good luck with your taxes!

Has anyone tried doing both TurboTax and H&R Block remote work in the same season? I'm thinking about applying to both to maximize hours.

I've been working remotely for TurboTax for three seasons now and thought I'd add some perspective on what to expect beyond just the scheduling and bonus structure. One thing that really surprised me was how much you learn about taxes in general - even if you're just doing customer support rather than actual tax preparation. By the end of my first season, I understood tax concepts I never knew existed and it actually helped with my own personal taxes. The workload can be intense during peak season (March-April), but the team support is generally good. Most managers understand that tax season is stressful for everyone and try to be accommodating when possible. A few practical tips if you do get hired: invest in a really comfortable headset since you'll be wearing it for hours, make sure your workspace is quiet (customers can hear background noise), and keep a notebook handy for jotting down common issues you encounter - it'll save you time later when similar situations come up. The work is seasonal but if you do well, they often invite you back the following year, and returning workers typically get first pick of schedules. Overall, it's been a solid way to earn extra income during tax season, just be prepared for some long days once things get busy!

This has been such a valuable discussion! I'm actually in a very similar situation with social casino winnings from different platforms, and I was completely overwhelmed trying to figure out the tax implications. The step-by-step approach everyone has outlined is brilliant - contact the platforms for detailed CSV transaction histories, calculate actual net losses, then compare itemized vs standard deduction based on real numbers rather than assumptions. I had no idea these social casinos kept such comprehensive records that they could provide in a usable format. What really convinced me to take this seriously is seeing the actual tax savings people achieved - $1,400 to $2,800 is nothing to sneeze at! And the documentation requirements seem much more reasonable than I initially feared, especially with the detailed platform records available. I'm definitely going to request those transaction histories this week. Even if I end up taking the standard deduction for simplicity, at least I'll know I made an informed decision based on the actual math rather than just guessing. Thanks to everyone who shared their real experiences navigating this - it's exactly the kind of practical guidance you need when dealing with these complex tax situations for the first time.

This entire discussion has been incredibly enlightening! As someone who's been lurking on tax forums trying to figure out my own social casino situation, this thread answered questions I didn't even know I should be asking. The methodical approach everyone has outlined is spot-on: get those detailed CSV transaction histories from the platforms, calculate your actual net gambling losses, then run the math on itemized vs standard deductions. What really impressed me is how several people achieved substantial tax savings ($1,400-$2,800) by taking the time to properly document their losses instead of just paying taxes on gross withdrawals. The documentation requirements seem much more manageable than I initially thought. Having the platforms provide comprehensive CSV files changes everything - it transforms what could be a nightmare of reconstructing records into a straightforward process of organizing existing data. For your specific situation with $33k in withdrawals, definitely start by contacting Modo and Crown Coins customer service for those complete transaction histories. If you deposited more than you withdrew (which sounds likely based on your comments about overall losses), those gambling losses combined with your other itemized deductions could result in significant tax savings. Either way, you're being smart to think this through carefully rather than just guessing at the best approach. Thanks to everyone who shared their real experiences - this kind of practical guidance from people who've actually navigated these issues is invaluable!