I went through something very similar last year and totally understand your confusion! Getting a 1099-NEC when you expected a W-2 is jarring, especially when your work situation sounds like a traditional employee setup. A few things to keep in mind as you navigate this: 1. **File correctly for now**: Even if you suspect misclassification, you'll need to report the 1099-NEC income on your tax return this year. Use Schedule C and don't forget Schedule SE for self-employment taxes. 2. **Track everything going forward**: Since others mentioned documentation - start keeping records of your work arrangements now. Things like email instructions, schedule requirements, use of company equipment, etc. 3. **Consider the bigger picture**: While the extra self-employment tax (around 15.3%) is frustrating, remember you can also deduct legitimate business expenses that employees can't. Keep receipts for anything work-related. 4. **You have time to decide**: You don't have to rush into filing Form SS-8 right now. You can file your taxes correctly based on the 1099-NEC you received, then evaluate your options for challenging the classification later if you decide it's worth pursuing. The most important thing right now is meeting your tax obligations while you figure out the classification issue. Don't let the stress of the bigger question prevent you from filing on time!

I really feel for you - this exact situation happened to me last year and it was so confusing! The good news is that you're not alone in dealing with this, and there are definitely steps you can take to figure it out. First, yes - receiving a 1099-NEC does mean the IRS will treat you as self-employed for tax purposes. You'll need to file Schedule C to report the income and Schedule SE for self-employment taxes (which is the extra ~15.3% others mentioned). But based on your description (set hours, using their equipment, being told exactly what to do), it really does sound like you might be misclassified. Here's what I wish someone had told me: you can file your taxes correctly with the 1099-NEC you received AND still challenge the classification later. Don't let the classification question prevent you from meeting your tax deadline - that's the most important thing right now. Start documenting everything about your work relationship immediately - emails about schedules, instructions about how to do your job, what equipment you're required to use, etc. This will be valuable whether you decide to file Form SS-8 or just want to have a conversation with your employer about the situation. Also, don't forget that being classified as self-employed does have one silver lining - you can deduct business expenses that regular employees can't. Keep track of anything work-related you pay for out of pocket. You've got this! Take it one step at a time and don't let the overwhelm paralyze you.

Quick question - does anyone know if state taxes work the same way for multiple jobs? I'm interning in a different state than my university, so I'll have income from two different states this year.

Great discussion everyone! As someone who went through this exact situation two years ago, I'd definitely recommend checking the multiple jobs box on your W4 for the internship. Even though the jobs don't overlap timing-wise, both incomes will appear on your 2025 tax return and could push you into a higher bracket. One thing I learned the hard way - don't forget to update your W4 again when you go back to your campus job in the fall! Since your internship will be over by then, you'll want to remove the multiple jobs designation for your fall semester campus work to avoid over-withholding. Also, keep good records of all your pay stubs from both jobs throughout the year. It makes tax filing so much easier when you have everything organized. The slight over-withholding during summer is usually worth avoiding a surprise tax bill in April!

I work for a state revenue department, and I can confirm that many of the strategies mentioned here are legitimate options, though they vary significantly by state. The key is acting before any titles are transferred. For assignment of prize rights, most states that recognize this require the assignment to be documented before you officially accept the prize. You can't retroactively assign something you've already claimed. The charity would typically need to be involved since they're the ones issuing the prize. Winner designation processes are less common but do exist in some states. These usually require forms to be filed with both the prize-issuing organization and sometimes with the state revenue department within a specific timeframe. One practical tip: when you call your state revenue office, ask specifically about "prize transfers to third parties" and "assignment of contest winnings." Don't just ask about general gift or sale tax rules - the specific language matters because these situations often have special provisions that regular customer service reps might not know about. Also, be prepared that even if your state allows these arrangements, the charity might have their own policies that prevent it. Some organizations have insurance or legal restrictions that require prizes to go directly to the actual winner, regardless of what state law allows. The good news is that most states recognize this double taxation issue and have some provision to address it, even if it's not well-publicized.

Based on all the excellent advice shared here, I'd recommend taking a systematic approach to your situation. First, contact the charity organization immediately to discuss your options - explain that you'd like to explore having the prize transferred directly to your friend to avoid double sales tax. Ask specifically about their policies on prize assignments or third-party transfers. While you're waiting for their response, call your state's revenue department and ask about "prize transfers to third parties" and "assignment of contest winnings" as Charlotte mentioned. This specific language will help you get connected to someone who knows the relevant regulations. If your state allows direct transfers and the charity is cooperative, you'll likely need to get everything documented before you officially claim or take possession of the vehicle. This timing is crucial - once you've accepted the prize formally, your options become much more limited. As a backup plan, research your state's "casual sale" exemptions that Isaiah mentioned, in case the direct transfer route isn't available. Some states do have provisions specifically designed to prevent the double taxation scenario you're facing. Remember that regardless of how you handle the vehicle transfer, you'll still owe federal income tax on the fair market value of the prize. The organization should send you a 1099-MISC for the car's value, which you'll need to report as income. Document everything throughout this process - your communications with the charity, your research into state regulations, and any official guidance you receive. This documentation will be invaluable for your tax filings and if any questions arise later. Good luck with your situation! With some advance planning, you should be able to avoid the double sales tax issue while still benefiting from your raffle win.

Has anyone used TurboTax for reporting timber sales? I'm wondering if the standard software can handle this or if I need something more specialized?

I dealt with a similar timber sale situation on my family's property a few years back. One thing I learned that wasn't mentioned yet - make sure to keep detailed records of any costs associated with the timber sale (road maintenance, marking trees, etc.) because these can be deducted from your gross proceeds when calculating your gain. Also, if you haven't already, consider getting a professional timber cruise done to establish current fair market value documentation. Even though your sale is complete, having this baseline can be helpful for future tax planning if you have more timber on the property. Some forestry consultants will do a retroactive valuation that can help support your basis calculations. The capital gains treatment really does make a huge difference - in my case it saved me about $8,000 compared to ordinary income rates. Just make sure you document everything well since timber sales sometimes get extra scrutiny during audits.

Has anyone successfully gotten their tax software to handle this correctly? I just gave up and hired a CPA because H&R Block kept trying to give me a massive refund when I honestly answered all the questions about my aunt's inherited IRA. The CPA charged me $375 just to fix this one issue!

I went through this exact same situation with my mother's IRA last year and completely understand your frustration! The key issue is that tax software often treats "inherited IRA" as if you're maintaining an inherited IRA account, but you actually took a full cash distribution. Here's what worked for me in TurboTax: Answer "Yes" to inheriting the IRA, but when it asks about the type of distribution, specifically look for an option like "I took a complete/total distribution" or "lump sum distribution." This should bypass the basis questions that are causing the software to calculate incorrectly. The reason you're seeing that massive refund is because the software is likely applying inheritance rules meant for people who are stretching distributions over time or who inherited Roth IRAs where distributions might be tax-free. Since your brother-in-law likely had a traditional IRA with pre-tax contributions (most common), the entire distribution should be taxable income. Make sure the distribution code in Box 7 of your 1099-R is correct - it should indicate death/inheritance (usually code 4). If everything is entered properly, you should pay ordinary income tax on the full amount with no early withdrawal penalty. Don't feel bad about being confused - this is one of the most poorly designed parts of tax software!