19 Has anyone actually been audited for this specific issue? I'm curious what happens in real life vs what's technically supposed to happen.

I went through this exact situation with a roofing contractor last year. After weeks of trying to get his W-9, I finally filed the 1099-NEC with "Applied For" in the TIN box (since I had made multiple documented attempts) and kept detailed records of every attempt to contact him. The key is documentation - save all your text messages, emails, and any other communication attempts. I created a simple log with dates and methods of contact. When I called the IRS directly, they confirmed that as long as you make reasonable efforts and document them, you're fulfilling your obligation. One thing that worked for me was sending a certified letter as a final attempt, stating that I was required by law to file the 1099 by January 31st with or without his information. Sometimes the formal letter gets their attention when texts and calls don't. The contractor actually called me back within a week of receiving it. Don't stress too much about this - the IRS understands that you can't force contractors to cooperate. What matters is that you're trying to comply with the law and have the documentation to prove it.

I've been using TurboTax for 8 years and never realized this was how they were getting my W2 info! I always thought it was because I had used them previously and they just saved my data from year to year. This actually explains why my husband's W2 info showed up automatically this year even though we're filing jointly for the first time. Learn something new every day lol.

This is actually a common concern that many taxpayers have when they first encounter TurboTax's auto-import feature. The system works through partnerships with major payroll processors like ADP, Paychex, and others. When your employer processes your W-2 through these services, the data becomes available in a shared database that TurboTax can access once you verify your identity. The key thing to understand is that you likely consented to this during account setup, though it's buried in the terms of service. The IRS also has regulations around this type of data sharing for tax preparation purposes, so it's not completely unregulated. If you're uncomfortable with this, you can disable the auto-import feature in your account settings under "Profile & Account" > "Import Settings." Just keep in mind you'll need to manually enter all your tax documents if you turn it off. Also worth checking this setting each year since TurboTax sometimes resets preferences when they update for the new tax season.

Just adding that if you're going to continue with FreeTaxUSA in future years, make sure you save a copy of this year's Form 6251 where your AMT prior depreciation will be calculated. That way next year you won't have this same problem. I switch tax software every couple years to find the best deal and I've learned to keep my own "tax transition document" with all the carryover values like capital loss carryovers, passive activity losses, AMT adjustments, etc.

This is such a common issue when switching tax software! I went through the exact same thing last year switching from TurboTax to FreeTaxUSA. The AMT prior depreciation is definitely buried in those forms, but once you find it, you'll be all set. One thing I'd add to the great advice already given - if you have multiple rental properties like I do, make sure you're getting the TOTAL cumulative AMT prior depreciation across all properties, not just one. It's easy to miss if you have properties acquired in different years with different depreciation schedules. Also, FreeTaxUSA's customer support is actually pretty good if you get really stuck. They helped me verify that I had entered the right amount when I was unsure. Much better than TurboTax's support in my experience, and you're not paying those crazy fees! Stick with the switch - it's worth the one-time hassle to save hundreds of dollars every year.

Does anyone know if Robinhood sends a physical copy of the W-9 form or is it filled out electronically? I'm dealing with the same issue but live in a dorm with unreliable mail.

Just wanted to add that you should keep detailed records of all your trades from the beginning, even the small ones. I wish someone had told me this when I started trading as a dependent student. Robinhood will provide you with a 1099-B form at tax time, but their cost basis reporting isn't always perfect, especially if you transfer stocks in from another broker or have wash sale situations. Having your own records makes tax time so much easier. Also, since you mentioned you're trading "for fun" - be aware that frequent trading might classify you as a "trader" rather than an "investor" for tax purposes, which has different rules. It's probably not a concern if you're just buying and holding some stocks, but something to keep in mind if you start day trading frequently. The W-9 is really no big deal though - just fill it out with your SSN and you'll be good to go!

Great question! I went through this exact situation last year. Based on what you've described - she brings her own supplies, sets her own schedule, and works independently - she sounds like an independent contractor rather than an employee. Since you've paid her $2,400 over 8 months ($150 × 2 × 8), you'll need to issue her a 1099-NEC because it's over the $600 threshold. You'll need her SSN or Tax ID number, and the form is due by January 31st for the previous tax year. The key factors the IRS looks at are: who controls when/how the work is done, who provides equipment/supplies, and whether they work for multiple clients. Your situation checks the contractor boxes. Just make sure to keep good records of payments and get her tax info before year-end!

I actually had this exact situation with my housekeeper last year and learned the hard way that the IRS looks at multiple factors beyond just supplies and scheduling. Even though my housekeeper brought her own supplies, the IRS agent I spoke with explained that since I was directing specific tasks (like "clean the bathrooms first, then kitchen") and she only worked for me regularly, she was actually classified as an employee. The determining factors aren't just about supplies - it's really about the degree of control you have over the work. If you're telling her what to clean, when to clean it, or how to do specific tasks, that leans toward employee status. If she's truly independent (you just say "clean the house" and she decides everything else), then contractor makes sense. I ended up having to file Schedule H and pay the household employment taxes retroactively. It was a pain, but better than dealing with penalties later. I'd recommend really carefully going through the IRS 20-factor test or getting professional advice before deciding, because the consequences of getting it wrong can be expensive.