Why did my boss give me both a W2 & 1099-NEC form for the same job?

What if the social media work was done during regular shifts? Like my manager would just tell me to "go post something" while I was on the clock as a server? Does that still count as contractor work?

If your manager was directing you to do social media work during your regular server shifts, that's a red flag. When the work is integrated into your regular duties, happens during your normal work hours, and your boss directly supervises what you're doing - that typically should all be W2 employment. For true contractor work, you should have significant independence in how and when you complete the tasks. It sounds like your situation might be what's called "misclassification," where an employer incorrectly treats regular employees as contractors to avoid paying taxes. You could consider talking to your employer first for clarification, or consult with a tax professional who might recommend filing Form SS-8 with the IRS to determine your correct worker status.

Does this thing actually work for figuring out if you're misclassified? My boss has me on a 1099 but controls literally everything about my job including what time I have to be there.

I'm a little skeptical... how is some AI supposed to know the details of tax law around contractor classification? Those rules are super complicated and depend on your specific situation. Did you end up having to confront your employer with this info?

Yes, it absolutely works for misclassification situations! The tool uses the same worker classification tests the IRS uses (like the control test, integration test, etc.) and asks you specific questions about your work arrangement. It then analyzes your answers against IRS guidelines and gives you a detailed breakdown. In my case, it showed my employer was incorrectly classifying me for certain duties where they maintained direct control. When I showed my employer the report, they actually thanked me because they didn't fully understand the rules themselves. They were worried about getting in trouble with the IRS and issued a corrected W2. The tool also has documentation explaining the tax implications for both you and your employer, which makes having that conversation much easier.

How does this Claimyr thing actually work? Seems sketchy that they can somehow magically get through to the IRS when nobody else can.

Yeah right. Nothing can get you through to the IRS faster. I've tried calling for THREE MONTHS about my identity theft issue and can't get a human. No way this actually works - probably just takes your money and tells you to keep holding.

It's not magic - they use a combination of technology and timing to navigate the IRS phone system. They basically call repeatedly using automated systems until they secure a spot in line, then they call you when they're about to connect with an agent. They know the best times to call and how to navigate the phone tree efficiently. I was skeptical too, but when you're desperate after trying for weeks, you'll try anything. I was actually shocked when they called me back and transferred me to an IRS agent who was already briefed on my issue. The agent confirmed I needed to file Form SS-8 to contest my worker classification and explained exactly how the process would work. It saved me literally dozens of hours of frustration.

I did last year. Had W2 for my bartending job and 1099 for DJing special events at the same venue. Made sure to document EVERYTHING for the 1099 work - kept mileage logs, receipts for equipment, music subscriptions, etc. Filed Schedule C with all those deductions. Ended up owing less than I expected! Just make sure you're setting aside money for taxes throughout the year.

Thanks for sharing your experience! That's really helpful to know it's doable without issues. Did you use any specific tax software that handled the dual arrangement well? I've been using TurboTax but wasn't sure if it would get confused with both forms from the same employer. I'll definitely start documenting my expenses better. I have some equipment purchases and mileage that should qualify for deductions. Did you pay quarterly estimated taxes on your 1099 income or just handle it all at filing time?

Thanks for the warning! Yeah, the social media stuff was definitely on their schedule - they'd just tell me to "go handle the Instagram during slow periods" of my server shift. I didn't even think about the payroll tax angle. Now I'm wondering if they're just trying to save money by putting some of my work on a 1099. Not cool.

This happened to me too! My accountant said it's actually illegal if they're controlling the work like that. I showed my boss the IRS guidelines and they fixed my classification. Saved me like $700 in self-employment taxes I shouldn't have had to pay.