This whole thread has been incredibly helpful! I had the exact same confusion with my E*Trade 1099-B and was leaning toward answer (b) before reading everyone's explanations. What really clicked for me was understanding that E*Trade is essentially doing the math for you behind the scenes. When they show that $839,230 cost basis, they've already factored in all the wash sale adjustments that happened throughout the year. So that $89,700 "Wash Sale Loss Disallowed" figure represents adjustments that are already reflected in your cost basis - it's not something you need to add separately. I think the confusion comes from the fact that this column exists at all. It feels like it should be part of the calculation somehow, but really it's just there for transparency so you can see how much in losses were disallowed during the tax year. Thanks to everyone who shared their experiences with E*Trade support, the IRS, and tax professionals. It's reassuring to see the same answer confirmed through multiple sources. I'm definitely going with the $37,220 realized gain amount when I file!

This has been such a valuable thread! I'm dealing with the exact same E*Trade 1099-B situation and was completely lost until reading everyone's explanations. What really helped me understand this was the analogy about the receipt - the "Wash Sale Loss Disallowed" column is like documentation showing what adjustments were made, but those adjustments are already incorporated into the cost basis figure. E*Trade has done all the heavy lifting by automatically adjusting the cost basis upward to account for disallowed wash sale losses. I was initially leaning toward answer (b) and adding the $89,700 to the realized gain, but now I clearly see that would be double-counting. The $37,220 realized gain is already the correct taxable amount because it's calculated using the wash-sale-adjusted cost basis. Thanks to everyone who called E*Trade support, used the IRS callback services, and shared their experiences with tax professionals. Having multiple independent confirmations of the same answer gives me confidence to file correctly. This community really came through with practical, actionable advice!

Word of warning about IRS Free File Fillable Forms that some people suggested: they're pretty buggy. I tried using them last year and ran into several glitches where calculations didn't transfer correctly between forms. I ended up having to redo everything in TurboTax anyway. If your return is simple, they might work fine, but for anything moderately complex (itemized deductions, multiple income sources, etc.) you might save yourself a headache by using proper tax software from the start.

Thanks everyone for all the helpful responses! This thread has been incredibly informative. I had no idea that the IRS doesn't accept PDF uploads directly - that would have saved me a lot of confusion from the start. Based on what I've read here, I think I'm going to try the taxr.ai service that @Jamal Wilson mentioned first, since it seems designed exactly for my situation of having already completed the forms. If that doesn't work out well, I'll fall back to either finding a local tax pro for review and e-filing (great suggestion @Fatima Al-Suwaidi) or just biting the bullet and re-entering everything into proper tax software. Really appreciate everyone taking the time to explain the technical limitations and share their experiences. This community is awesome!

I'm so sorry you're dealing with this frustrating situation! Federal agency internships can be really confusing tax-wise. One thing I'd add to the excellent advice already given - make sure you're tracking your mileage for any work-related travel during the internship period. The IRS standard mileage rate for 2023 was 65.5 cents per mile, so even short trips to pick up supplies or attend meetings can add up to meaningful deductions. Also, since you mentioned working unpaid overtime, if you had to purchase any meals during those extended work hours (like grabbing dinner because you were working late), those might qualify as deductible business meals at 50% of the cost. Keep any receipts you still have! For future reference, it's worth documenting everything in real-time when you're in these gray-area employment situations. I learned this lesson the hard way too. Good luck getting through this - the self-employment learning curve is steep but you'll figure it out!

This whole situation sounds incredibly frustrating, and unfortunately it's more common than it should be with federal internships. The lack of proper documentation from your agency is really problematic, but you're on the right track with Schedule C. A few additional deductions you might want to consider that haven't been mentioned yet: - Professional clothing or uniforms required specifically for this internship - Any books, journals, or research materials you purchased for your work - Parking fees at the federal facility (if applicable) - Any software licenses beyond Adobe that you needed - Professional association memberships if required for your field - Bank fees related to setting up accounts for your stipend payments Since you mentioned working in a different state, don't forget that you might need to file state returns in both your home state and the state where you worked. Some states have reciprocity agreements, but others don't. One more thing - document everything thoroughly and keep copies of all your records. Federal agencies sometimes get audited more frequently, and having solid documentation will protect you if questions arise later. The IRS is generally understanding about situations like yours where the employer doesn't provide proper documentation, as long as you're reporting the income accurately and can substantiate your deductions. Hang in there - this experience will make you much more tax-savvy for any future self-employment situations!

Connor, you're definitely on the right track with Scenario 2! I went through a very similar situation last year with multiple betting platforms and can confirm that you aggregate all your gambling activities together when filing taxes. Your math is correct - you'd report $24,500 in total gambling winnings as income, then deduct $21,300 in total losses if you itemize deductions. This results in $3,200 of net taxable gambling income, which is much better than paying taxes on the full $7,800 from FanDuel alone. The key decision you'll need to make is whether itemizing deductions is worth it for your overall tax situation. You'll need your total itemized deductions (gambling losses plus mortgage interest, state taxes, charitable donations, etc.) to exceed the standard deduction for your filing status. If they don't, you'd unfortunately have to pay taxes on the full $24,500 in winnings even though your actual profit was only $3,200. I'd recommend running the numbers both ways before deciding how to file. Also, make sure to download comprehensive records from both FanDuel and DraftKings - including any detailed transaction histories they provide - since good documentation is crucial for gambling deductions. The annual statements are usually sufficient, but having backup records gives you extra peace of mind if you ever face an audit. Good luck with your filing, and definitely consider setting up a simple tracking system going forward to make next year's taxes easier!

Connor, everyone here has given you excellent advice about aggregating your gambling winnings and losses across platforms. I just wanted to add one practical tip that saved me a lot of headaches when I was in a similar situation. Since you're right on the edge where the itemization decision could make or break your tax strategy, I'd recommend using tax software or consulting with a tax professional to run both scenarios (itemizing vs. standard deduction) before you file. The difference in your tax liability could be substantial - potentially thousands of dollars depending on your other deductions. Also, for future reference, consider keeping a simple running tally of your gambling losses throughout the year. This helps you make more informed decisions about your betting activity and whether you're likely to benefit from itemizing when tax time comes around. If you know early in the year that you're going to be itemizing anyway, you can plan other deductible expenses accordingly. One last thing - make sure to keep digital copies of all your records in multiple places (cloud storage, email, etc.). I learned this the hard way when one of my betting platforms changed their record retention policy and I almost lost access to some transaction history. Better safe than sorry when it comes to IRS documentation!

I'm also navigating this as someone relatively new to the US tax system, and I wanted to add something that helped me understand the bigger picture. The W9 is part of what's called "backup withholding" prevention. Essentially, if the bank doesn't have your correct taxpayer identification number (SSN) on file, they're required by law to withhold 24% of any interest or other payments they make to you and send it directly to the IRS. By filling out the W9 correctly, you're preventing this automatic withholding. Even though you don't have income right now, this protects you if the account ever earns interest in the future. Without the W9, that 24% would be automatically withheld from any interest payments, and you'd have to claim it back when filing taxes - which is just unnecessary paperwork and hassle. So think of the W9 as protecting your future self from automatic tax withholding, rather than creating any new tax obligations. It's actually working in your favor by ensuring you keep control over your money rather than having the bank automatically send portions to the IRS. This perspective helped me feel better about all the banking paperwork when I was getting established here. Hope it helps you too!

I want to add another perspective that might help ease your concerns about the W9 - this is actually one of the simpler tax-related forms you'll encounter in the US system! The W9 is basically just asking for information the bank already has about you anyway: your name, address, and SSN. There are no complex calculations, no income reporting, and no decisions to make about deductions or filing status. You're literally just confirming information that's already in your file. As someone who has been through the US immigration process, I can tell you that compared to the paperwork you've probably already dealt with for your SSN application and immigration documentation, the W9 is refreshingly straightforward. It's a single page that takes about 2 minutes to complete. The fact that you're asking these thoughtful questions shows you're being appropriately careful, but don't let the unfamiliarity of the US system make this seem more complicated than it is. Once you fill it out and submit it, you'll probably wonder why you were worried about such a simple form! Keep that same careful approach as you learn the US tax system, but know that this particular step is one of the easier ones you'll encounter.