just a heads up - i did an SS-8 filing last year and it took almost 9 months to get a determination letter! the irs is super backed up with these. definitely file your taxes now using form 8919 like others said. also make sure you keep copies of EVERYTHING. every email, every instruction they gave her, work schedule, etc. the more proof you have that they treated her like an employee the better.

One more thing to consider - if this was a government agency, there's a good chance they have specific policies about contractor vs employee classification that they're supposed to follow. Federal agencies in particular have gotten in trouble for misclassifying workers to avoid paying benefits and taxes. You might want to look up whether this agency has had previous issues with worker misclassification. Sometimes there are patterns, and if the agency has been cited before, it could strengthen your case. The Government Accountability Office (GAO) has done reports on this issue across various federal agencies. Also, since you mentioned they haven't sent any tax documents yet, that's actually a red flag. Even if they classified her as a contractor, they're legally required to send a 1099-NEC by January 31st if they paid her more than $600. I'd follow up on that immediately - you'll need that information regardless of how you file. Good luck with the SS-8 process! It sounds like you have a strong case based on what you've described.

For TurboTax specifically, here's how I entered my 1099-K without an EIN last year: 1. In the Income section, select "I'll tell you what I did" (not the guided experience) 2. Choose "Business" 3. On the business income screen, select that you received a 1099-K 4. Enter your gross amount from Box 1a 5. When asked for business info, just enter your name and use your SSN where it asks for tax ID 6. Make sure to enter all business expenses on the next screens The software handles it perfectly fine without an EIN. Just be thorough with documenting expenses like those Square fees!

Friendly reminder that Square fees aren't your only potential deduction! When I got my first 1099-K, I only deducted the processing fees and ended up paying WAY too much in taxes. Don't forget about: - Supplies for your services - Any equipment purchases - Mileage if you travel to clients - Portion of phone bill if used for business - Software subscriptions related to your work - Continuing education or training costs - Marketing/advertising expenses TurboTax walks through all these categories, so don't skip them! Your tax bill could be significantly lower.

Has anyone dealt with scholarship money in this situation? My daughter gets a partial scholarship that covers about 60% of her tuition. I pay the rest plus all living expenses. I'm worried this complicates the "providing more than half support" calculation.

Just wanted to add my experience to help others in similar situations. My 19-year-old son is in his second year of college and works about 20 hours a week at a local restaurant. He makes around $15,000 annually, but I still cover tuition, room and board, health insurance, and his car payment - which adds up to way more than what he earns. The key thing I learned is to keep good records of what you're paying for throughout the year. I track all the major expenses like tuition payments, housing costs, food allowances, insurance premiums, etc. This makes it much easier to prove you're providing more than half their support if the IRS ever questions it. Also, don't forget about the education credits! Since I claim him as a dependent, I'm eligible for the American Opportunity Credit which can be worth up to $2,500 per year. That's a huge tax benefit that makes claiming him as a dependent even more valuable than just the dependent exemption alone. My son files his own return and gets back most of what was withheld from his paychecks, and I get the dependent benefits plus education credits. It really is a win-win situation when done correctly.

Just a heads up - make sure you're looking at your actual W-2 to confirm the ESPP discount is really included there. Some companies handle this differently! My company actually doesn't include the ESPP discount in the W-2 for disqualifying dispositions - instead they report it on a separate 3922 form and I have to report it as "Other Income" when I file. Worth double-checking how your specific company handles it so you don't make incorrect adjustments.

This thread has been incredibly helpful! I'm dealing with a similar ESPP situation and was totally confused about the basis adjustments. One thing I'd add for anyone else reading this - if you have multiple ESPP purchases throughout the year at different discount rates, make sure you're tracking the specific discount amount for each lot separately. My company's supplemental statement breaks this down by purchase date, which is crucial since the 15% discount applies to different FMV amounts depending on when you bought. Also, don't forget that if you had any dividend reinvestments on your ESPP shares before selling, those might affect your basis calculation too. I almost missed that detail until I noticed some small amounts on my brokerage statement. Thanks everyone for sharing your experiences - this stuff is way more complex than it should be!

Does anyone know if you actually NEED to make this election for small rental property repairs? I've been reading that if all your repair expenses are under $2,500 per invoice, you might qualify to deduct them outright as repairs without making this formal election. I'm using Cash App Taxes too and can't figure out where to put this election statement, so I'm wondering if I can just skip it and still deduct my minor expenses.

I actually had this exact same issue with Cash App Taxes last year! After trying multiple approaches, I found the solution in an unexpected place. Go to your Schedule E section, select the specific rental property you're working on, then look for a section called "Property Details" or "Additional Property Information." Within that section, there should be a text field for "Notes" or "Comments" - it's usually near the bottom and easy to miss. I put my de minimis safe harbor election statement there using this language: "Taxpayer elects the de minimis safe harbor under Treasury Regulation Section 1.263(a)-3(h) for all eligible expenditures for the tax year ending December 31, 2024." My return was accepted without any issues, and I've used this same approach for two years now. The key is that the election needs to be associated with your rental property reporting, which Schedule E accomplishes perfectly. If you still can't find that field, try updating Cash App Taxes - they've moved some sections around in recent updates. Hope this helps!