I totally understand the panic you're feeling! I went through something similar when I was setting up my consulting business last year. I actually made an even more embarrassing mistake - I accidentally wrote my personal SSN instead of leaving it blank for the business entity section and didn't catch it until after I'd already faxed it. From what I've learned through that experience and talking to other small business owners, the IRS is surprisingly forgiving with these kinds of administrative oversights on SS4 forms. The date field, while included on the form, isn't one of the critical elements that would cause an automatic rejection. The key things they really care about are having a complete signature, accurate business information, and proper entity classification. As long as you've got those covered (which it sounds like you do), you should be in good shape. My recommendation would be to wait about 2-3 weeks and then call to check on the status rather than immediately resubmitting. That way you can confirm they received it and are processing it normally. If for some reason there is an issue, they can guide you on the best way to handle it at that point. Don't beat yourself up too much about this - these forms can be tricky even when you're being super careful. The fact that you triple-checked everything else shows you were being thorough. Best of luck with your new side business!

Hey Sarah! I totally get that sinking feeling when you realize you missed something important on official paperwork. I went through a similar panic when I submitted my SS4 form for my freelance business and realized I had made a mistake with one of the fields. From everything I've read and experienced, the missing date really shouldn't be a deal-breaker for your EIN application. The IRS processes thousands of these forms and they're much more concerned with having your signature (which validates your authority to request the EIN) and complete business information than they are about the date field. That said, I understand wanting certainty, especially when you need that EIN for your bank account. My suggestion would be to wait about 2-3 weeks before taking any action. If you haven't heard anything by then, call the IRS Business & Specialty Tax Line to check on your application status rather than immediately resubmitting. This way you can confirm they received it and avoid any potential confusion from duplicate submissions. I know the waiting is stressful when you're eager to get your business up and running, but try not to stress too much about this particular mistake. You clearly put a lot of care into getting everything else right, and that attention to detail will serve you well as you grow your side business. Good luck!

I can completely relate to this worry! I went through the exact same panic when I started helping my elderly parents with their finances through Cash App. I was depositing cash from my own savings to help them pay bills online, and I was terrified I'd created some kind of tax mess. After researching extensively and even calling the IRS (took forever to get through!), I learned that what we're doing is completely normal and not taxable at all. You're essentially just digitizing physical cash you already own - it's no different from depositing cash at an ATM into your regular bank account. The key thing to remember is that the IRS distinguishes between "your own money" and "income from others." When you deposit your pocket money into Cash App, you're just moving YOUR money from one form to another. No new income is being created, so there's nothing to tax. The $600 threshold for 1099-K forms only applies to payments you RECEIVE from other people for selling goods or providing services. Your own deposits don't count toward this at all. So even if you deposited $5,000 of your own cash, that wouldn't trigger any tax reporting as long as you weren't also receiving payments from others. You're being a good family member helping out, and you definitely don't need to stress about the tax implications of these deposits!

I just wanted to chime in as someone who was in almost the exact same situation! I was depositing my own cash into Cash App to help my roommates with shared expenses, and I was so worried about whether I'd accidentally created taxable income. After doing a lot of research and talking to my accountant during tax season, I can confirm what everyone else is saying - depositing your own physical cash into Cash App is absolutely not a taxable event. You're not earning new income, you're just converting cash you already had into digital form. The easiest way I learned to think about it is this: imagine you had $850 in your wallet and you went to your bank and deposited it. Would that be taxable? No way! Cash App works the same way - it's just a digital wallet instead of a physical bank account. The $850 you've deposited over the past few months is still the same $850 you had before, just in a different format. Since it was your money to begin with, there's no new income being created and nothing for the IRS to tax. You can rest easy knowing you haven't messed anything up tax-wise!

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!

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!

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!