This is a really common issue that many former international students face! I went through something very similar with Wells Fargo a few years ago. The key thing to understand is that banks often don't have staff who are well-trained on the distinction between different tax forms for non-residents. When you call back, be very clear and persistent: "I am a non-resident alien living permanently outside the United States. I need to complete form W-8BEN, not W-9. The W-9 is only for US persons, which I am not." You might need to escalate to a supervisor or their international banking department. Also, keep in mind that once you submit the correct W-8BEN form, the bank will likely withhold 30% tax on any interest earned (unless your home country has a tax treaty with the US that reduces this rate). This is normal for non-resident accounts and much better than accidentally being classified as a US person for tax purposes. Don't let them pressure you into the wrong form just because it's easier for their system!

I've been dealing with a very similar situation with my TD Bank account after moving back to the UK. The confusion around W-9 vs W-8BEN is incredibly common, and banks often default to requesting W-9s because it's what they're most familiar with. Here's what worked for me: I called and specifically asked to speak with someone in their "international accounts" or "non-resident banking" department. Regular customer service reps often aren't trained on these distinctions. When I explained that I was a non-resident alien who needed to file W-8BEN instead of W-9, they knew exactly what I was talking about and sent me the correct form immediately. Also worth noting - make sure you have documentation of your current foreign address ready when you call. They'll need to verify your non-resident status, and having utility bills or bank statements from your home country can help speed up the process. The W-8BEN will properly classify you as a non-resident alien and allow you to claim any applicable tax treaty benefits between your home country and the US. Much better than accidentally being classified as a US person who needs to file annual returns!

As someone who's been doing delivery driving for a while, I'd suggest starting simple for your first year. Track your phone usage for a typical week or two to establish a baseline business percentage - don't just guess. For a $1350 iPhone used part-time for deliveries, you're probably looking at somewhere between 20-40% business use realistically. The key is being able to defend your percentage if questioned. Keep records of your delivery hours, and consider that business use includes not just active delivery time but also time spent checking for orders, navigating, and communicating with customers. For TurboTax, you'll enter this on Schedule C under "Other expenses" and create a line item for "Cell phone (business portion)". The software will walk you through whether to depreciate or take the immediate deduction based on your usage percentage. One tip: don't forget you can also deduct things like a phone mount for your car, charging cables you use while driving, and even a portion of your phone case if you bought it specifically for delivery work protection. These smaller items add up!

Great question about phone deductions! Just wanted to add a few practical tips from my experience doing gig work taxes: For tracking business vs personal use, I recommend keeping it simple but defensible. When you're actively logged into the delivery app and available for orders, that's clearly business time - even if you're multitasking with personal stuff. The IRS understands that modern phones are used for multiple purposes simultaneously. A reasonable approach is to calculate total hours you were "on shift" (logged into UberEats and available) versus total phone usage time. You don't need to track every minute perfectly, but having some logical basis helps. For your iPhone, since you only worked Oct-Dec 2024, make sure to prorate the deduction for partial year use. So if you calculate 30% business use, you'd take 30% of the phone cost, then multiply by 3/12 (the portion of the year you were working). Also remember that the monthly payments you're making can be deducted as they're paid, using the same business percentage. So each month you make a payment, you can deduct the business portion of that payment. Keep good records and be conservative but reasonable with your estimates. The IRS expects some judgment calls with mixed-use items like phones.

Hey Isaiah! You're smart to ask about this early. Just want to emphasize what others have said - definitely report those gains even if they seem small. The IRS has been cracking down on unreported investment income lately, especially from popular apps like Cash App. One thing I haven't seen mentioned yet is that you might also want to look into whether you need to make estimated quarterly tax payments going forward if you plan to keep trading. If your investment gains are significant next year, you could owe penalties for underpayment if you don't pay taxes throughout the year. Also, since you're new to this, consider keeping a simple spreadsheet of your trades as backup documentation. Include buy date, sell date, stock symbol, shares, and amounts. It'll make next year's taxes much easier and gives you peace of mind if there are any discrepancies with your 1099-B. Welcome to the world of investment taxes - it gets easier once you've done it a few times!

Hey Isaiah! Looks like you've gotten some great advice here already. As someone who's been through this exact situation, I just wanted to add one more thing that might help - if you're feeling overwhelmed by all the tax forms and calculations, don't hesitate to use tax software like TurboTax, FreeTaxUSA, or H&R Block online. They all have sections specifically for investment income and will walk you through entering your 1099-B information step by step. The software will automatically calculate whether your gains are short-term or long-term based on the dates you enter, and it'll populate all the right forms (Schedule D and Form 8949) for you. Since your gains are under $1,000, this should be pretty straightforward even for a first-timer. One last tip - when you do get your 1099-B from Cash App, don't panic if it looks complicated with lots of transactions. The tax software will import most of the data automatically if you upload a PDF of the form, which saves tons of time compared to entering each trade manually. Good luck!

This is such a helpful thread for beginners! I'm also new to trading and had the exact same confusion about how losses work when you're profitable overall. One thing I wanted to add that might help other newcomers - don't forget that your state might have different rules for capital gains taxes too. I'm in California and was surprised to learn that they don't give preferential treatment to long-term capital gains like the federal government does. So even if you hold stocks for over a year, California still taxes those gains as regular income. It's worth checking your state's specific rules since this can make a big difference in your overall tax planning strategy. Some states have no capital gains tax at all, while others treat it the same as ordinary income regardless of how long you held the investment. Also, totally agree with everyone saying to keep your own records! My broker's 1099-B had my cost basis wrong on a stock I transferred from another account, and having my own spreadsheet saved me from overpaying on taxes.

This thread has been incredibly helpful! I'm also a beginner trader and had the exact same confusion about how losses offset gains when you're profitable overall. One thing I learned recently that might help others - make sure to understand the difference between realized and unrealized gains/losses. Only trades you actually completed (bought AND sold) count for tax purposes. If you're holding stocks that are down but haven't sold them yet, those paper losses can't offset your realized gains for tax purposes. I made this mistake in my planning earlier this year - I thought my unrealized losses would help reduce my tax bill, but then realized I'd actually have to sell those positions before year-end to capture the losses. Just something to keep in mind as we approach the end of the year! Also echoing what others said about keeping your own records. I use a simple Google Sheet and it's been a lifesaver when reviewing my broker statements. Takes just a minute per trade but gives you so much more confidence when tax time comes around.

I've been using OLT for the past two years and it's been solid for my situation. I have W-2 income plus some freelance work and investment accounts, so not super simple but not crazy complex either. The biggest adjustment coming from TurboTax was the interface - it's definitely more bare-bones and doesn't hold your hand as much. But honestly, once you get used to it, it's actually faster to navigate because there's less fluff. The federal filing being completely free regardless of complexity is huge - I was paying like $120+ with TurboTax for the same forms. One thing to watch out for - their error checking isn't as robust as the bigger names, so definitely review everything carefully before submitting. I caught a couple small mistakes on my own that might have been flagged automatically in TurboTax. But for the price difference, it's worth the extra attention to detail. Customer service is decent if you need it, though not as polished as what you'd get with premium services. Overall, I'd recommend giving it a shot - worst case, you can always fall back to TurboTax if you run into issues, but I think you'll find it handles your situation just fine.

I've been following this thread and it's really helpful hearing everyone's experiences with OLT! I'm in a similar boat as Pedro - been using TurboTax forever but the cost keeps going up every year. One thing I haven't seen mentioned much is how OLT handles estimated quarterly payments if you have side gig income. Does anyone know if they provide the vouchers and calculate the amounts for next year's estimated payments like TurboTax does? That's been really convenient for my freelance work and I'd hate to lose that feature. Also, for those who made the switch - did you feel confident that your refund/tax owed amount was calculated correctly? I know some of you mentioned doing side-by-side comparisons, but I'm curious if anyone felt like they got a significantly different result between the two platforms that made them question the accuracy.