Just wanted to add that I work with a lot of small business clients, and most of the time the IRS will process the SS4 form without the date as long as it's signed. The signature is what legally matters most. However, the IRS is currently experiencing significant processing delays for paper forms - we're seeing 4-6 week waits for EINs submitted by fax or mail.

I had almost the exact same situation last month! Forgot to date my SS4 form and was panicking about it. I ended up calling the IRS Business line (used that Claimyr service someone mentioned to avoid the hold time nightmare) and the agent told me they received my form and were processing it despite the missing date. She explained that as long as the form is signed and all the key business information is complete, they'll usually process it. The date field is more for their internal tracking than a requirement for approval. My EIN came through about 5 weeks later, so you should be fine! I'd recommend calling to confirm they received it rather than sending a duplicate form, just to avoid any potential confusion in their system.

Wait I'm confused about something else with Cash App. If I send money to my mom through Cash App to help with bills (like $300/month), does she have to pay taxes on that? It's not for any services, just family support.

Just to add some clarity for anyone else reading this - the key distinction here is between deposits and income. When you deposit your own physical cash into Cash App, you're not creating new income, you're just changing the form of money you already have. It's like converting a $20 bill into four $5 bills - the value doesn't change and there's no tax event. The IRS cares about the SOURCE of funds, not the METHOD of storing them. So whether you keep cash in your wallet, deposit it in a bank account, or load it onto Cash App, there's no difference from a tax perspective. Cash App will only send you a 1099-K if you RECEIVE payments for goods or services totaling more than $600 in a year. This is completely separate from your own deposits. Keep good records of what money is yours versus what you receive from others, and you'll be fine when tax season comes around.

Something nobody has mentioned yet - if you're using TurboTax, you can actually import your E*Trade 1099-B electronically rather than manually entering everything. When you do this, TurboTax automatically handles all the wash sale calculations correctly based on how E*Trade reports them. I've done this for the past three years and it's saved me tons of time and worry. The import function correctly recognizes that E*Trade's Realized Gain already includes the wash sale adjustments.

For anyone facing E*Trade 1099-B wash sale reporting issues, here's what I learned after calling E*Trade's tax support line: 1) The Realized Gain on your 1099-B ($37,220 in your case) is ALREADY the correct taxable amount 2) The Wash Sale Loss Disallowed amount is shown separately just for informational purposes 3) E*Trade has already adjusted your Cost Basis by adding back the disallowed wash sales 4) Adding the Wash Sale Loss Disallowed to your Realized Gain would be DOUBLE COUNTING I literally spent hours researching this last year and ended up calling E*Trade directly. Their tax specialist confirmed this is how their 1099-Bs work. Hope this helps!

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!

Make sure you're setting aside money for estimated quarterly tax payments going forward if you're continuing as self-employed. Getting hit with penalties for underpayment really sucks! I learned this the hard way.

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!